NPASS Compound

Structure

NPC41679 OpenBabel07101719522D 43 50 0 0 1 0 0 0 0 0999 V2000 3.6154 -0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5703 -1.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3946 -0.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2681 -2.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9516 0.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7688 -2.3415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9439 1.5403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9095 1.3874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5403 -0.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3312 -0.3692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8858 -0.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9135 0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0099 -3.2351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4566 -1.7537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3741 0.2768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1633 -3.7240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1712 -2.4316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1529 0.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3436 -2.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7088 -1.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6232 -0.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1506 -1.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5747 -0.7910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4842 0.5964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2835 -0.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0099 -2.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7365 -1.6033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6232 -1.2798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7765 -1.7686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3388 -0.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3166 -2.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1633 -1.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9298 -0.3021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9298 -1.2798 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7765 0.1867 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3166 -3.2351 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3665 -0.8123 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5936 -2.2534 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.4348 0.8246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2558 -1.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2305 0.9977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 27 2 0 0 0 0 14 19 1 0 0 0 0 14 30 1 0 0 0 0 15 36 1 0 0 0 0 16 37 2 0 0 0 0 17 39 1 0 0 0 0 18 40 1 0 0 0 0 19 39 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 22 29 2 0 0 0 0 22 36 1 0 0 0 0 23 35 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 6 0 0 0 25 41 2 0 0 0 0 26 42 1 0 0 0 0 27 28 1 0 0 0 0 27 33 1 0 0 0 0 28 31 2 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 30 35 1 1 0 0 0 31 38 1 0 0 0 0 32 33 2 0 0 0 0 32 37 1 0 0 0 0 33 38 1 0 0 0 0 34 35 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 35 21 1 1 0 0 0 36 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.34
Volume:	609.39
LogP:	3.27
LogD:	2.427
LogS:	-3.387
# Rotatable Bonds:	1
TPSA:	92.69
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	6.609
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.388
MDCK Permeability:	1.608352795301471e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.349
Plasma Protein Binding (PPB):	86.69477844238281%
Volume Distribution (VD):	6.064
Pgp-substrate:	12.495737075805664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.211
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	8.7
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.924
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.921
Carcinogencity:	0.394
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.954

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC41679

Natural Product ID:	NPC41679
*Common Name:**	GNVMYASVHYRDQY-BHUZSFBASA-N
IUPAC Name:	n.a.
Synonyms:	6-Hydroxymanzamine E
Standard InCHIKey:	GNVMYASVHYRDQY-BHUZSFBASA-N
Standard InCHI:	InChI=1S/C36H44N4O3/c41-25-8-7-18-40-24(9-10-25)21-35-23-39-17-6-4-2-1-3-5-15-36(43,34(35)40)22-29(30(35)14-19-39)32-33-27(13-16-37-32)28-20-26(42)11-12-31(28)38-33/h1,3,11-13,16,20,22,24,30,34,38,42-43H,2,4-10,14-15,17-19,21,23H2/b3-1-/t24-,30-,34+,35-,36-/m0/s1
SMILES:	O=C1CCCN2[C@@H](CC1)C[C@]13[C@@H]2[C@]2(O)CC/C=CCCCCN(C1)CC[C@H]3C(=C2)c1nccc2c1[nH]c1c2cc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502434
PubChem CID:	21585550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	11
MIC	3
Others	3

Activity Type	# Activity
Cell Line	2
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	Activity	=	4.3	ug ml-1	PMID[471033]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4.3	ug.mL-1	PMID[471034]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.78	ug.mL-1	PMID[471033]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.87	ug.mL-1	PMID[471033]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2.5	ug.mL-1	PMID[471033]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	5.5	ug.mL-1	PMID[471033]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	3.5	ug.mL-1	PMID[471033]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	4.3	ug.mL-1	PMID[471033]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.4	ug.mL-1	PMID[471033]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.4	ug.mL-1	PMID[471034]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.78	ug.mL-1	PMID[471034]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.87	ug.mL-1	PMID[471034]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2.5	ug.mL-1	PMID[471034]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	5.5	ug.mL-1	PMID[471034]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	3.5	ug.mL-1	PMID[471034]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	4.3	ug.mL-1	PMID[471034]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	52070.0	nM	PMID[471035]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC41679 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	514
0.1-0.2	2422
0.2-0.3	12831
0.3-0.4	16817
0.4-0.5	5327
0.5-0.6	2380
0.6-0.7	1937
0.7-0.8	440
0.8-0.85	17
0.85-0.9	6
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC473312
0.9387	High Similarity	NPC6215
0.919	High Similarity	NPC473310
0.8991	High Similarity	NPC476451
0.8839	High Similarity	NPC81175
0.8636	High Similarity	NPC475338
0.8636	High Similarity	NPC909
0.8565	High Similarity	NPC471891
0.8538	High Similarity	NPC473362
0.8538	High Similarity	NPC166492
0.8525	High Similarity	NPC476041
0.8525	High Similarity	NPC304926
0.8514	High Similarity	NPC475258
0.843	Intermediate Similarity	NPC476491
0.8357	Intermediate Similarity	NPC475070
0.8349	Intermediate Similarity	NPC250835
0.8246	Intermediate Similarity	NPC265576
0.8202	Intermediate Similarity	NPC207686
0.8165	Intermediate Similarity	NPC5145
0.8155	Intermediate Similarity	NPC295452
0.8155	Intermediate Similarity	NPC171393
0.8125	Intermediate Similarity	NPC471506
0.8065	Intermediate Similarity	NPC475288
0.8054	Intermediate Similarity	NPC473757
0.8037	Intermediate Similarity	NPC476116
0.8035	Intermediate Similarity	NPC326363
0.7991	Intermediate Similarity	NPC477861
0.7974	Intermediate Similarity	NPC325976
0.7948	Intermediate Similarity	NPC476492
0.7946	Intermediate Similarity	NPC469727
0.7917	Intermediate Similarity	NPC45459
0.7917	Intermediate Similarity	NPC315491
0.7913	Intermediate Similarity	NPC253580
0.7902	Intermediate Similarity	NPC472027
0.7902	Intermediate Similarity	NPC469928
0.7899	Intermediate Similarity	NPC178858
0.787	Intermediate Similarity	NPC470126
0.7863	Intermediate Similarity	NPC295228
0.7863	Intermediate Similarity	NPC477549
0.7841	Intermediate Similarity	NPC276657
0.7834	Intermediate Similarity	NPC213308
0.7834	Intermediate Similarity	NPC249040
0.7824	Intermediate Similarity	NPC192315
0.7808	Intermediate Similarity	NPC476098
0.7788	Intermediate Similarity	NPC476167
0.7763	Intermediate Similarity	NPC211813
0.7757	Intermediate Similarity	NPC99666
0.7749	Intermediate Similarity	NPC319232
0.7749	Intermediate Similarity	NPC24370
0.7696	Intermediate Similarity	NPC77555
0.7696	Intermediate Similarity	NPC156704
0.7689	Intermediate Similarity	NPC171171
0.7679	Intermediate Similarity	NPC184225
0.7674	Intermediate Similarity	NPC324149
0.7665	Intermediate Similarity	NPC251936
0.7655	Intermediate Similarity	NPC477610
0.7652	Intermediate Similarity	NPC74619
0.7642	Intermediate Similarity	NPC314002
0.7632	Intermediate Similarity	NPC27041
0.763	Intermediate Similarity	NPC220765
0.7615	Intermediate Similarity	NPC232130
0.7613	Intermediate Similarity	NPC471564
0.7613	Intermediate Similarity	NPC470500
0.7607	Intermediate Similarity	NPC314954
0.7602	Intermediate Similarity	NPC478080
0.76	Intermediate Similarity	NPC471304
0.7598	Intermediate Similarity	NPC264285
0.7595	Intermediate Similarity	NPC97902
0.7594	Intermediate Similarity	NPC204717
0.7591	Intermediate Similarity	NPC176538
0.7589	Intermediate Similarity	NPC477111
0.7588	Intermediate Similarity	NPC183407
0.7586	Intermediate Similarity	NPC229893
0.7583	Intermediate Similarity	NPC477066
0.7576	Intermediate Similarity	NPC60621
0.7572	Intermediate Similarity	NPC17437
0.7565	Intermediate Similarity	NPC193267
0.7565	Intermediate Similarity	NPC213530
0.7553	Intermediate Similarity	NPC323752
0.7552	Intermediate Similarity	NPC478081
0.7552	Intermediate Similarity	NPC478082
0.7552	Intermediate Similarity	NPC477067
0.7545	Intermediate Similarity	NPC88008
0.7533	Intermediate Similarity	NPC219087
0.7531	Intermediate Similarity	NPC15801
0.7522	Intermediate Similarity	NPC477714
0.7521	Intermediate Similarity	NPC60006
0.752	Intermediate Similarity	NPC476493
0.7511	Intermediate Similarity	NPC330009
0.7511	Intermediate Similarity	NPC101543
0.7511	Intermediate Similarity	NPC252338
0.7511	Intermediate Similarity	NPC469554
0.75	Intermediate Similarity	NPC53534
0.75	Intermediate Similarity	NPC477113
0.7478	Intermediate Similarity	NPC477715
0.747	Intermediate Similarity	NPC315467
0.7469	Intermediate Similarity	NPC63971
0.7469	Intermediate Similarity	NPC91868
0.7468	Intermediate Similarity	NPC162748
0.7467	Intermediate Similarity	NPC270918
0.7459	Intermediate Similarity	NPC469734
0.7458	Intermediate Similarity	NPC33949
0.7449	Intermediate Similarity	NPC153400
0.7446	Intermediate Similarity	NPC96321
0.7446	Intermediate Similarity	NPC477609
0.7443	Intermediate Similarity	NPC276517
0.7442	Intermediate Similarity	NPC62749
0.7441	Intermediate Similarity	NPC184964
0.7436	Intermediate Similarity	NPC130570
0.7435	Intermediate Similarity	NPC477110
0.7434	Intermediate Similarity	NPC171787
0.7411	Intermediate Similarity	NPC223427
0.7411	Intermediate Similarity	NPC98715
0.7409	Intermediate Similarity	NPC11445
0.7407	Intermediate Similarity	NPC473540
0.7407	Intermediate Similarity	NPC39092
0.7404	Intermediate Similarity	NPC245348
0.7404	Intermediate Similarity	NPC476818
0.7401	Intermediate Similarity	NPC271862
0.7395	Intermediate Similarity	NPC15102
0.7393	Intermediate Similarity	NPC280272
0.7393	Intermediate Similarity	NPC16352
0.7391	Intermediate Similarity	NPC237740
0.7389	Intermediate Similarity	NPC53344
0.7386	Intermediate Similarity	NPC28945
0.7384	Intermediate Similarity	NPC477608
0.7376	Intermediate Similarity	NPC227582
0.7373	Intermediate Similarity	NPC478010
0.7373	Intermediate Similarity	NPC478009
0.7373	Intermediate Similarity	NPC214980
0.7371	Intermediate Similarity	NPC478006
0.7364	Intermediate Similarity	NPC195239
0.7364	Intermediate Similarity	NPC157828
0.7357	Intermediate Similarity	NPC127677
0.7357	Intermediate Similarity	NPC258062
0.7355	Intermediate Similarity	NPC101350
0.7354	Intermediate Similarity	NPC329793
0.735	Intermediate Similarity	NPC310118
0.735	Intermediate Similarity	NPC473317
0.7347	Intermediate Similarity	NPC81939
0.7345	Intermediate Similarity	NPC175602
0.7342	Intermediate Similarity	NPC478078
0.7336	Intermediate Similarity	NPC208284
0.7333	Intermediate Similarity	NPC53144
0.7333	Intermediate Similarity	NPC200836
0.7327	Intermediate Similarity	NPC46580
0.7325	Intermediate Similarity	NPC61038
0.7323	Intermediate Similarity	NPC152620
0.7322	Intermediate Similarity	NPC477112
0.7317	Intermediate Similarity	NPC475666
0.7314	Intermediate Similarity	NPC235685
0.7313	Intermediate Similarity	NPC46225
0.7313	Intermediate Similarity	NPC225821
0.7311	Intermediate Similarity	NPC311906
0.7311	Intermediate Similarity	NPC477607
0.7304	Intermediate Similarity	NPC87856
0.7304	Intermediate Similarity	NPC151976
0.7304	Intermediate Similarity	NPC110182
0.7304	Intermediate Similarity	NPC472098
0.7302	Intermediate Similarity	NPC48938
0.7294	Intermediate Similarity	NPC213629
0.7294	Intermediate Similarity	NPC32771
0.7294	Intermediate Similarity	NPC321708
0.7293	Intermediate Similarity	NPC167860
0.7293	Intermediate Similarity	NPC475422
0.7293	Intermediate Similarity	NPC123976
0.7292	Intermediate Similarity	NPC475720
0.7292	Intermediate Similarity	NPC474192
0.7291	Intermediate Similarity	NPC478083
0.7284	Intermediate Similarity	NPC203614
0.7284	Intermediate Similarity	NPC8022
0.7284	Intermediate Similarity	NPC204491
0.7284	Intermediate Similarity	NPC470799
0.7284	Intermediate Similarity	NPC132211
0.728	Intermediate Similarity	NPC329982
0.7277	Intermediate Similarity	NPC474896
0.7273	Intermediate Similarity	NPC471080
0.7273	Intermediate Similarity	NPC469592
0.7273	Intermediate Similarity	NPC267965
0.7269	Intermediate Similarity	NPC476121
0.7269	Intermediate Similarity	NPC476124
0.7265	Intermediate Similarity	NPC131887
0.7261	Intermediate Similarity	NPC220852
0.7257	Intermediate Similarity	NPC476138
0.7257	Intermediate Similarity	NPC245816
0.7257	Intermediate Similarity	NPC125597
0.7246	Intermediate Similarity	NPC31097
0.7244	Intermediate Similarity	NPC300183
0.7243	Intermediate Similarity	NPC285343
0.7243	Intermediate Similarity	NPC88363
0.7241	Intermediate Similarity	NPC478157
0.724	Intermediate Similarity	NPC307963
0.7234	Intermediate Similarity	NPC472099
0.7231	Intermediate Similarity	NPC478011
0.7231	Intermediate Similarity	NPC478012
0.7231	Intermediate Similarity	NPC182222
0.7229	Intermediate Similarity	NPC294620
0.7229	Intermediate Similarity	NPC26543
0.7227	Intermediate Similarity	NPC132631
0.7227	Intermediate Similarity	NPC214142

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC41679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	586
0.2-0.3	745
0.3-0.4	1777
0.4-0.5	2682
0.5-0.6	2065
0.6-0.7	952
0.7-0.8	79
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7991	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD484	Approved
0.7826	Intermediate Similarity	NPD7603	Discontinued
0.7804	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7948	Phase 1
0.7623	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7112	Discontinued
0.7572	Intermediate Similarity	NPD8358	Approved
0.7555	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD7666	Phase 3
0.7511	Intermediate Similarity	NPD7665	Phase 2
0.7456	Intermediate Similarity	NPD3330	Phase 1
0.7455	Intermediate Similarity	NPD5426	Phase 3
0.7435	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6242	Discontinued
0.738	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8093	Discontinued
0.7353	Intermediate Similarity	NPD7824	Approved
0.7347	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7470	Discontinued
0.7333	Intermediate Similarity	NPD7952	Approved
0.7333	Intermediate Similarity	NPD7951	Approved
0.7333	Intermediate Similarity	NPD4886	Phase 2
0.7333	Intermediate Similarity	NPD7950	Approved
0.7333	Intermediate Similarity	NPD7953	Approved
0.7333	Intermediate Similarity	NPD7789	Approved
0.7333	Intermediate Similarity	NPD7791	Approved
0.7333	Intermediate Similarity	NPD7790	Approved
0.7315	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5612	Discontinued
0.7281	Intermediate Similarity	NPD2916	Discontinued
0.7281	Intermediate Similarity	NPD6376	Discontinued
0.7273	Intermediate Similarity	NPD6530	Approved
0.7273	Intermediate Similarity	NPD6531	Approved
0.7269	Intermediate Similarity	NPD7731	Approved
0.7269	Intermediate Similarity	NPD7730	Approved
0.7264	Intermediate Similarity	NPD5065	Approved
0.7254	Intermediate Similarity	NPD8016	Phase 3
0.7254	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD1038	Approved
0.7238	Intermediate Similarity	NPD5559	Phase 2
0.7232	Intermediate Similarity	NPD8395	Approved
0.7232	Intermediate Similarity	NPD6999	Discontinued
0.7232	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8396	Approved
0.7232	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8101	Phase 3
0.7225	Intermediate Similarity	NPD5901	Discontinued
0.7222	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8094	Discontinued
0.7197	Intermediate Similarity	NPD4845	Discontinued
0.7189	Intermediate Similarity	NPD4558	Phase 2
0.7185	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7271	Approved
0.7173	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7924	Phase 2
0.7171	Intermediate Similarity	NPD7925	Phase 2
0.7162	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4038	Approved
0.7149	Intermediate Similarity	NPD4035	Approved
0.7149	Intermediate Similarity	NPD4039	Approved
0.7149	Intermediate Similarity	NPD3746	Discontinued
0.7149	Intermediate Similarity	NPD4033	Approved
0.7149	Intermediate Similarity	NPD31	Approved
0.7149	Intermediate Similarity	NPD4037	Approved
0.7149	Intermediate Similarity	NPD4034	Approved
0.7149	Intermediate Similarity	NPD32	Approved
0.7149	Intermediate Similarity	NPD4036	Approved
0.7149	Intermediate Similarity	NPD4122	Approved
0.7125	Intermediate Similarity	NPD6165	Phase 2
0.7125	Intermediate Similarity	NPD6164	Phase 2
0.7119	Intermediate Similarity	NPD7415	Suspended
0.7114	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8100	Phase 3
0.7095	Intermediate Similarity	NPD7780	Approved
0.7095	Intermediate Similarity	NPD7781	Approved
0.7093	Intermediate Similarity	NPD4511	Phase 1
0.7085	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4885	Approved
0.7077	Intermediate Similarity	NPD8363	Approved
0.7077	Intermediate Similarity	NPD8364	Approved
0.7074	Intermediate Similarity	NPD4795	Phase 2
0.7068	Intermediate Similarity	NPD3959	Phase 2
0.7068	Intermediate Similarity	NPD3962	Phase 2
0.7059	Intermediate Similarity	NPD8091	Phase 3
0.7054	Intermediate Similarity	NPD7618	Phase 3
0.7054	Intermediate Similarity	NPD8430	Approved
0.7054	Intermediate Similarity	NPD7619	Phase 3
0.7048	Intermediate Similarity	NPD4600	Approved
0.7048	Intermediate Similarity	NPD4601	Approved
0.7047	Intermediate Similarity	NPD8247	Approved
0.7047	Intermediate Similarity	NPD8246	Approved
0.7037	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2091	Phase 2
0.7032	Intermediate Similarity	NPD2096	Phase 2
0.7029	Intermediate Similarity	NPD8356	Approved
0.7023	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7222	Phase 2
0.7004	Intermediate Similarity	NPD8426	Approved
0.7004	Intermediate Similarity	NPD8425	Approved
0.7	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3394	Approved
0.6992	Remote Similarity	NPD3393	Approved
0.6992	Remote Similarity	NPD3389	Approved
0.6988	Remote Similarity	NPD6456	Discontinued
0.6986	Remote Similarity	NPD2095	Phase 2
0.6986	Remote Similarity	NPD2094	Phase 2
0.6986	Remote Similarity	NPD2092	Phase 2
0.6981	Remote Similarity	NPD8428	Approved
0.6981	Remote Similarity	NPD8429	Approved
0.6981	Remote Similarity	NPD8427	Approved
0.6975	Remote Similarity	NPD3402	Phase 1
0.6972	Remote Similarity	NPD6595	Phase 3
0.697	Remote Similarity	NPD7001	Phase 3
0.6966	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7221	Approved
0.6958	Remote Similarity	NPD7219	Approved
0.6957	Remote Similarity	NPD5482	Discontinued
0.6955	Remote Similarity	NPD6178	Phase 3
0.6948	Remote Similarity	NPD424	Approved
0.6948	Remote Similarity	NPD425	Approved
0.6944	Remote Similarity	NPD482	Approved
0.6937	Remote Similarity	NPD8431	Approved
0.6933	Remote Similarity	NPD802	Phase 2
0.6929	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7181	Phase 3
0.6923	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8467	Approved
0.6917	Remote Similarity	NPD7726	Phase 1
0.6917	Remote Similarity	NPD8466	Approved
0.6917	Remote Similarity	NPD8465	Approved
0.6916	Remote Similarity	NPD5003	Discontinued
0.6914	Remote Similarity	NPD8442	Discontinued
0.6911	Remote Similarity	NPD7558	Phase 2
0.691	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5658	Approved
0.691	Remote Similarity	NPD2509	Approved
0.691	Remote Similarity	NPD2510	Approved
0.6907	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1739	Approved
0.69	Remote Similarity	NPD1740	Approved
0.6897	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7957	Phase 1
0.6897	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5530	Phase 1
0.6894	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3404	Approved
0.6886	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8370	Discontinued
0.6872	Remote Similarity	NPD7426	Phase 1
0.6872	Remote Similarity	NPD6352	Phase 2
0.6872	Remote Similarity	NPD8289	Discontinued
0.6872	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4442	Phase 2
0.687	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3006	Discontinued
0.6851	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3013	Phase 3
0.6851	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6978	Phase 2
0.6844	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7944	Discontinued
0.6827	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8349	Phase 1
0.6824	Remote Similarity	NPD3809	Discontinued
0.6823	Remote Similarity	NPD8524	Approved
0.682	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8459	Approved
0.6815	Remote Similarity	NPD8460	Approved
0.6814	Remote Similarity	NPD6665	Discontinued
0.681	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7923	Phase 2
0.6807	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4897	Phase 2
0.6806	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7711	Discontinued
0.68	Remote Similarity	NPD4499	Approved
0.6795	Remote Similarity	NPD7452	Approved
0.6795	Remote Similarity	NPD7453	Approved
0.6792	Remote Similarity	NPD4429	Discontinued
0.6792	Remote Similarity	NPD3354	Phase 2
0.6792	Remote Similarity	NPD6568	Discontinued
0.6792	Remote Similarity	NPD5255	Approved
0.679	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8512	Phase 3
0.6789	Remote Similarity	NPD6969	Phase 2
0.6789	Remote Similarity	NPD6968	Phase 2
0.6786	Remote Similarity	NPD3961	Discontinued
0.6786	Remote Similarity	NPD6141	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data