NPASS Compound

Structure

NPC473362 OpenBabel07101718182D 41 48 0 0 1 0 0 0 0 0999 V2000 6.5284 -2.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4832 -3.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4352 -1.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3078 -2.2860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1814 -3.9728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0093 -0.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5880 -2.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1914 -2.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7942 -1.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8652 -1.8753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6826 -4.3129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9739 -0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3781 -2.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6173 -3.6775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8229 -1.8931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9203 -5.2056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3718 -3.7257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2883 -1.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0745 -5.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 -4.4029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7640 -1.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2589 -4.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9168 -3.5541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5372 -2.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0662 -3.8143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3427 -2.7640 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.6461 -3.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9203 -4.2289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5372 -3.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6914 -3.7406 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.2488 -2.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2287 -4.2289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0745 -3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8456 -2.2757 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8456 -3.2523 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.6914 -1.7874 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.2287 -5.2056 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.2776 -2.7853 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5087 -4.2249 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.9168 -1.9739 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.1459 -0.9772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 26 1 0 0 0 0 14 27 2 0 0 0 0 15 31 2 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 18 36 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 40 1 0 0 0 0 22 39 1 0 0 0 0 23 26 1 0 0 0 0 23 35 1 0 0 0 0 24 29 2 0 0 0 0 24 36 1 0 0 0 0 25 35 1 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 33 2 0 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 30 35 1 0 0 0 0 31 38 1 0 0 0 0 32 33 1 0 0 0 0 32 37 2 0 0 0 0 33 38 1 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 36 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.35
Volume:	591.809
LogP:	5.28
LogD:	4.105
LogS:	-3.451
# Rotatable Bonds:	1
TPSA:	55.39
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.326
Synthetic Accessibility Score:	6.503
Fsp3:	0.528
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.127
MDCK Permeability:	2.175851841457188e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.503

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917
Plasma Protein Binding (PPB):	95.48053741455078%
Volume Distribution (VD):	2.532
Pgp-substrate:	4.179325103759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.294
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.154
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.149
CYP2D6-inhibitor:	0.991
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.739

ADMET: Excretion

Clearance (CL):	5.3
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.916
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.416
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.945
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC473362

Natural Product ID:	NPC473362
*Common Name:**	Manzamine A Hcl
IUPAC Name:	n.a.
Synonyms:	Manzamine A HCl
Standard InCHIKey:	DIVWQABXFSWTEF-YTGAITGWSA-N
Standard InCHI:	InChI=1S/C36H44N4O.ClH/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33;/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2;1H/b4-1-,13-7-;/t26-,30-,34+,35-,36-;/m0./s1
SMILES:	O[C@@]12CC/C=CCCCCN3C[C@]4([C@H]2N2CCCCC=C[C@H]2C4)[C@H](C(=C1)c1nccc2c1[nH]c1c2cccc1)CC3.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403027
PubChem CID:	49797386 9894648
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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]

☑ 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	1
MIC	1
Others	9

Activity Type	# Activity
Cell Line	9
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	0.6	ug ml-1	PMID[458262]
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.0067	ug ml-1	PMID[458262]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	0.36	ug ml-1	PMID[458262]
NPT575	Cell Line	KM-20L2	Homo sapiens	Activity	=	0.37	ug ml-1	PMID[458262]
NPT1081	Cell Line	BXPC-3	Homo sapiens	Activity	=	0.35	ug ml-1	PMID[458262]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.41	ug ml-1	PMID[458262]
NPT395	Cell Line	SF-268	Homo sapiens	Activity	=	0.42	ug ml-1	PMID[458262]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.7	ug.mL-1	PMID[458262]
NPT616	Cell Line	MDCK	Canis lupus familiaris	Papp	=	1.9	10'-6 cm/s	PMID[458263]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	99.0	%	PMID[458262]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	ug.mL-1	PMID[458262]

☑ 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 NPC473362 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	578
0.1-0.2	2803
0.2-0.3	20968
0.3-0.4	11216
0.4-0.5	3045
0.5-0.6	2087
0.6-0.7	1502
0.7-0.8	461
0.8-0.85	15
0.85-0.9	9
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC166492
0.9632	High Similarity	NPC250835
0.9457	High Similarity	NPC265576
0.9282	High Similarity	NPC473310
0.9275	High Similarity	NPC473757
0.9179	High Similarity	NPC472027
0.911	High Similarity	NPC475288
0.9104	High Similarity	NPC6215
0.9045	High Similarity	NPC471506
0.8878	High Similarity	NPC476451
0.8824	High Similarity	NPC476492
0.8789	High Similarity	NPC232130
0.8732	High Similarity	NPC476491
0.8592	High Similarity	NPC909
0.8592	High Similarity	NPC475338
0.8551	High Similarity	NPC475258
0.8538	High Similarity	NPC41679
0.8433	Intermediate Similarity	NPC471891
0.8372	Intermediate Similarity	NPC81175
0.8333	Intermediate Similarity	NPC473312
0.8333	Intermediate Similarity	NPC251936
0.8263	Intermediate Similarity	NPC15102
0.8227	Intermediate Similarity	NPC471564
0.8117	Intermediate Similarity	NPC476493
0.8116	Intermediate Similarity	NPC304926
0.8116	Intermediate Similarity	NPC476041
0.8088	Intermediate Similarity	NPC475422
0.8079	Intermediate Similarity	NPC87755
0.7947	Intermediate Similarity	NPC59269
0.7931	Intermediate Similarity	NPC475070
0.7927	Intermediate Similarity	NPC472294
0.7895	Intermediate Similarity	NPC280852
0.7876	Intermediate Similarity	NPC48938
0.7839	Intermediate Similarity	NPC133366
0.7828	Intermediate Similarity	NPC477861
0.7819	Intermediate Similarity	NPC317430
0.7766	Intermediate Similarity	NPC213629
0.7766	Intermediate Similarity	NPC160105
0.774	Intermediate Similarity	NPC126066
0.7736	Intermediate Similarity	NPC477714
0.7734	Intermediate Similarity	NPC303820
0.7734	Intermediate Similarity	NPC23420
0.7734	Intermediate Similarity	NPC205254
0.7734	Intermediate Similarity	NPC106771
0.7729	Intermediate Similarity	NPC314957
0.7727	Intermediate Similarity	NPC95783
0.7725	Intermediate Similarity	NPC63751
0.7714	Intermediate Similarity	NPC475602
0.77	Intermediate Similarity	NPC474177
0.7696	Intermediate Similarity	NPC314603
0.7696	Intermediate Similarity	NPC475935
0.7696	Intermediate Similarity	NPC94211
0.7696	Intermediate Similarity	NPC472123
0.7696	Intermediate Similarity	NPC52909
0.7689	Intermediate Similarity	NPC477715
0.7688	Intermediate Similarity	NPC92796
0.7688	Intermediate Similarity	NPC135141
0.7672	Intermediate Similarity	NPC474561
0.7672	Intermediate Similarity	NPC49954
0.7665	Intermediate Similarity	NPC62749
0.7656	Intermediate Similarity	NPC5145
0.765	Intermediate Similarity	NPC324149
0.7632	Intermediate Similarity	NPC201700
0.7622	Intermediate Similarity	NPC80597
0.7622	Intermediate Similarity	NPC70922
0.7622	Intermediate Similarity	NPC212376
0.7622	Intermediate Similarity	NPC75540
0.7622	Intermediate Similarity	NPC211572
0.7608	Intermediate Similarity	NPC476116
0.7598	Intermediate Similarity	NPC100321
0.7588	Intermediate Similarity	NPC65215
0.7588	Intermediate Similarity	NPC173028
0.758	Intermediate Similarity	NPC314954
0.7577	Intermediate Similarity	NPC151939
0.7576	Intermediate Similarity	NPC94752
0.7568	Intermediate Similarity	NPC259644
0.7568	Intermediate Similarity	NPC73952
0.7568	Intermediate Similarity	NPC469763
0.7568	Intermediate Similarity	NPC469760
0.7568	Intermediate Similarity	NPC469786
0.7568	Intermediate Similarity	NPC25008
0.7568	Intermediate Similarity	NPC469765
0.7566	Intermediate Similarity	NPC317105
0.7565	Intermediate Similarity	NPC329688
0.7565	Intermediate Similarity	NPC189812
0.7553	Intermediate Similarity	NPC279918
0.7549	Intermediate Similarity	NPC473640
0.7549	Intermediate Similarity	NPC192315
0.7549	Intermediate Similarity	NPC171317
0.7538	Intermediate Similarity	NPC317030
0.7538	Intermediate Similarity	NPC204565
0.7526	Intermediate Similarity	NPC203754
0.7526	Intermediate Similarity	NPC150048
0.7524	Intermediate Similarity	NPC475506
0.7513	Intermediate Similarity	NPC472108
0.7513	Intermediate Similarity	NPC19679
0.7513	Intermediate Similarity	NPC139291
0.7513	Intermediate Similarity	NPC282231
0.7512	Intermediate Similarity	NPC293917
0.7512	Intermediate Similarity	NPC476167
0.75	Intermediate Similarity	NPC300688
0.75	Intermediate Similarity	NPC321708
0.7488	Intermediate Similarity	NPC155143
0.7488	Intermediate Similarity	NPC157828
0.7488	Intermediate Similarity	NPC195314
0.7488	Intermediate Similarity	NPC195239
0.7487	Intermediate Similarity	NPC474707
0.7487	Intermediate Similarity	NPC469785
0.7486	Intermediate Similarity	NPC63545
0.7477	Intermediate Similarity	NPC183407
0.7475	Intermediate Similarity	NPC284678
0.7474	Intermediate Similarity	NPC194640
0.7473	Intermediate Similarity	NPC325903
0.7462	Intermediate Similarity	NPC314394
0.7462	Intermediate Similarity	NPC233936
0.746	Intermediate Similarity	NPC131718
0.746	Intermediate Similarity	NPC229173
0.7459	Intermediate Similarity	NPC24678
0.7459	Intermediate Similarity	NPC105818
0.7452	Intermediate Similarity	NPC98715
0.7451	Intermediate Similarity	NPC11445
0.745	Intermediate Similarity	NPC17059
0.7449	Intermediate Similarity	NPC215795
0.7449	Intermediate Similarity	NPC176199
0.7449	Intermediate Similarity	NPC133261
0.7447	Intermediate Similarity	NPC469762
0.7447	Intermediate Similarity	NPC129721
0.7446	Intermediate Similarity	NPC469811
0.7446	Intermediate Similarity	NPC201380
0.7446	Intermediate Similarity	NPC179787
0.7441	Intermediate Similarity	NPC271862
0.7441	Intermediate Similarity	NPC162860
0.744	Intermediate Similarity	NPC300183
0.7429	Intermediate Similarity	NPC54420
0.7421	Intermediate Similarity	NPC253580
0.7421	Intermediate Similarity	NPC16667
0.7416	Intermediate Similarity	NPC470500
0.7416	Intermediate Similarity	NPC470505
0.7415	Intermediate Similarity	NPC229332
0.7409	Intermediate Similarity	NPC280548
0.7409	Intermediate Similarity	NPC194411
0.7407	Intermediate Similarity	NPC230869
0.7407	Intermediate Similarity	NPC221786
0.7407	Intermediate Similarity	NPC475990
0.7407	Intermediate Similarity	NPC474880
0.7405	Intermediate Similarity	NPC321911
0.7404	Intermediate Similarity	NPC193761
0.7398	Intermediate Similarity	NPC326575
0.7396	Intermediate Similarity	NPC54988
0.7394	Intermediate Similarity	NPC285469
0.7391	Intermediate Similarity	NPC252338
0.7385	Intermediate Similarity	NPC474896
0.7382	Intermediate Similarity	NPC311276
0.7378	Intermediate Similarity	NPC295228
0.7376	Intermediate Similarity	NPC231536
0.7376	Intermediate Similarity	NPC470126
0.7373	Intermediate Similarity	NPC213530
0.7373	Intermediate Similarity	NPC193267
0.7368	Intermediate Similarity	NPC81229
0.7368	Intermediate Similarity	NPC255229
0.7358	Intermediate Similarity	NPC478158
0.7352	Intermediate Similarity	NPC31097
0.7352	Intermediate Similarity	NPC162748
0.7352	Intermediate Similarity	NPC155444
0.7346	Intermediate Similarity	NPC46225
0.7346	Intermediate Similarity	NPC225821
0.7342	Intermediate Similarity	NPC33949
0.7337	Intermediate Similarity	NPC472110
0.7337	Intermediate Similarity	NPC159856
0.7337	Intermediate Similarity	NPC472109
0.7336	Intermediate Similarity	NPC151976
0.7336	Intermediate Similarity	NPC87856
0.7336	Intermediate Similarity	NPC75634
0.7336	Intermediate Similarity	NPC31385
0.7336	Intermediate Similarity	NPC110602
0.7336	Intermediate Similarity	NPC75726
0.733	Intermediate Similarity	NPC470203
0.7326	Intermediate Similarity	NPC470233
0.732	Intermediate Similarity	NPC474897
0.7318	Intermediate Similarity	NPC229893
0.7316	Intermediate Similarity	NPC56765
0.7316	Intermediate Similarity	NPC67056
0.7311	Intermediate Similarity	NPC127677
0.7311	Intermediate Similarity	NPC258062
0.731	Intermediate Similarity	NPC68354
0.7309	Intermediate Similarity	NPC477175
0.7309	Intermediate Similarity	NPC470730
0.7309	Intermediate Similarity	NPC326363
0.7308	Intermediate Similarity	NPC249040
0.7302	Intermediate Similarity	NPC221100
0.7302	Intermediate Similarity	NPC234078
0.7302	Intermediate Similarity	NPC267965
0.7296	Intermediate Similarity	NPC275305
0.7296	Intermediate Similarity	NPC37423
0.7295	Intermediate Similarity	NPC131887
0.7292	Intermediate Similarity	NPC40779
0.7292	Intermediate Similarity	NPC102423
0.729	Intermediate Similarity	NPC320968
0.7285	Intermediate Similarity	NPC313884
0.7285	Intermediate Similarity	NPC98371

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 NPC473362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	552
0.2-0.3	1009
0.3-0.4	1848
0.4-0.5	2541
0.5-0.6	1903
0.6-0.7	917
0.7-0.8	105
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8263	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5065	Approved
0.7882	Intermediate Similarity	NPD4886	Phase 2
0.7772	Intermediate Similarity	NPD6595	Phase 3
0.7716	Intermediate Similarity	NPD8431	Approved
0.7706	Intermediate Similarity	NPD7824	Approved
0.763	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7731	Approved
0.7615	Intermediate Similarity	NPD7730	Approved
0.7604	Intermediate Similarity	NPD7271	Approved
0.7592	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7665	Phase 2
0.756	Intermediate Similarity	NPD7666	Phase 3
0.7523	Intermediate Similarity	NPD7953	Approved
0.7523	Intermediate Similarity	NPD7791	Approved
0.7523	Intermediate Similarity	NPD7950	Approved
0.7523	Intermediate Similarity	NPD7951	Approved
0.7523	Intermediate Similarity	NPD7789	Approved
0.7523	Intermediate Similarity	NPD7790	Approved
0.7523	Intermediate Similarity	NPD7952	Approved
0.7512	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7948	Phase 1
0.75	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4181	Approved
0.7476	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3404	Approved
0.7473	Intermediate Similarity	NPD2837	Discontinued
0.745	Intermediate Similarity	NPD3961	Discontinued
0.745	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3330	Phase 1
0.7416	Intermediate Similarity	NPD5426	Phase 3
0.7409	Intermediate Similarity	NPD6352	Phase 2
0.7407	Intermediate Similarity	NPD5255	Approved
0.7382	Intermediate Similarity	NPD3323	Discontinued
0.7361	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4076	Approved
0.736	Intermediate Similarity	NPD4079	Approved
0.7358	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD8093	Discontinued
0.7317	Intermediate Similarity	NPD7618	Phase 3
0.7317	Intermediate Similarity	NPD7619	Phase 3
0.731	Intermediate Similarity	NPD3505	Approved
0.731	Intermediate Similarity	NPD3506	Approved
0.731	Intermediate Similarity	NPD2144	Approved
0.7299	Intermediate Similarity	NPD7957	Phase 1
0.7299	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7469	Discontinued
0.7296	Intermediate Similarity	NPD4128	Approved
0.7286	Intermediate Similarity	NPD3038	Discontinued
0.7285	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8386	Phase 2
0.7273	Intermediate Similarity	NPD2172	Phase 1
0.7265	Intermediate Similarity	NPD7780	Approved
0.7265	Intermediate Similarity	NPD7781	Approved
0.726	Intermediate Similarity	NPD6999	Discontinued
0.726	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1325	Approved
0.7231	Intermediate Similarity	NPD1326	Approved
0.7228	Intermediate Similarity	NPD706	Phase 1
0.722	Intermediate Similarity	NPD6165	Phase 2
0.722	Intermediate Similarity	NPD6164	Phase 2
0.722	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6978	Phase 2
0.7214	Intermediate Similarity	NPD6178	Phase 3
0.7209	Intermediate Similarity	NPD7470	Discontinued
0.7198	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1722	Approved
0.717	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4547	Phase 3
0.7166	Intermediate Similarity	NPD4703	Approved
0.7166	Intermediate Similarity	NPD4702	Approved
0.7164	Intermediate Similarity	NPD2092	Phase 2
0.7164	Intermediate Similarity	NPD2095	Phase 2
0.7164	Intermediate Similarity	NPD2094	Phase 2
0.7163	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7112	Discontinued
0.715	Intermediate Similarity	NPD4999	Phase 3
0.715	Intermediate Similarity	NPD4998	Phase 3
0.7143	Intermediate Similarity	NPD8094	Discontinued
0.7143	Intermediate Similarity	NPD4601	Approved
0.7143	Intermediate Similarity	NPD4600	Approved
0.713	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2091	Phase 2
0.7129	Intermediate Similarity	NPD2096	Phase 2
0.7123	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7423	Phase 2
0.7122	Intermediate Similarity	NPD6281	Approved
0.7121	Intermediate Similarity	NPD482	Approved
0.7116	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7867	Phase 1
0.7108	Intermediate Similarity	NPD8021	Approved
0.7108	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8020	Approved
0.7094	Intermediate Similarity	NPD3082	Discontinued
0.7092	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5901	Discontinued
0.7089	Intermediate Similarity	NPD8272	Phase 2
0.7087	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2380	Approved
0.7085	Intermediate Similarity	NPD2382	Approved
0.7085	Intermediate Similarity	NPD4075	Phase 2
0.7085	Intermediate Similarity	NPD2381	Approved
0.7083	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3013	Phase 3
0.7075	Intermediate Similarity	NPD8073	Approved
0.7072	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7415	Suspended
0.7053	Intermediate Similarity	NPD4615	Phase 2
0.705	Intermediate Similarity	NPD8123	Approved
0.705	Intermediate Similarity	NPD8122	Approved
0.7037	Intermediate Similarity	NPD3100	Discontinued
0.7037	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8408	Discontinued
0.7028	Intermediate Similarity	NPD5017	Discontinued
0.7026	Intermediate Similarity	NPD5140	Approved
0.7026	Intermediate Similarity	NPD5138	Approved
0.7024	Intermediate Similarity	NPD7394	Phase 2
0.7023	Intermediate Similarity	NPD8322	Phase 2
0.702	Intermediate Similarity	NPD3610	Approved
0.702	Intermediate Similarity	NPD3609	Approved
0.701	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6849	Phase 2
0.7009	Intermediate Similarity	NPD6850	Phase 2
0.7005	Intermediate Similarity	NPD4640	Approved
0.7005	Intermediate Similarity	NPD4639	Approved
0.7005	Intermediate Similarity	NPD5913	Phase 3
0.7005	Intermediate Similarity	NPD4638	Approved
0.7005	Intermediate Similarity	NPD5862	Discovery
0.7005	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6958	Approved
0.7	Intermediate Similarity	NPD5100	Phase 3
0.7	Intermediate Similarity	NPD3830	Phase 1
0.7	Intermediate Similarity	NPD6664	Approved
0.7	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6957	Approved
0.6995	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5596	Phase 2
0.6991	Remote Similarity	NPD4612	Discontinued
0.699	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.699	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.699	Remote Similarity	NPD2720	Phase 1
0.6986	Remote Similarity	NPD7944	Discontinued
0.6982	Remote Similarity	NPD3402	Phase 1
0.6977	Remote Similarity	NPD7001	Phase 3
0.6973	Remote Similarity	NPD786	Approved
0.6963	Remote Similarity	NPD8072	Approved
0.6963	Remote Similarity	NPD2882	Phase 1
0.6961	Remote Similarity	NPD4957	Phase 2
0.6959	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8063	Discontinued
0.6955	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD424	Approved
0.6954	Remote Similarity	NPD425	Approved
0.6952	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3717	Discontinued
0.6952	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7711	Discontinued
0.6947	Remote Similarity	NPD7603	Discontinued
0.6942	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5428	Discontinued
0.6933	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8321	Discontinued
0.6927	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6711	Approved
0.6919	Remote Similarity	NPD2641	Approved
0.6919	Remote Similarity	NPD2640	Approved
0.6919	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4462	Approved
0.6911	Remote Similarity	NPD4463	Approved
0.6906	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4602	Approved
0.6902	Remote Similarity	NPD198	Clinical (unspecified phase)
0.69	Remote Similarity	NPD750	Phase 2
0.6895	Remote Similarity	NPD1661	Suspended

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