NPASS Compound

Structure

CID79402 OpenBabel06191715412D 31 34 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 27 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 19 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 2 1 6 0 0 0 15 27 1 0 0 0 0 16 3 1 6 0 0 0 16 22 1 0 0 0 0 16 27 1 0 0 0 0 17 23 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 29 1 0 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 25 2 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	421.23
Volume:	449.092
LogP:	5.21
LogD:	3.476
LogS:	-5.438
# Rotatable Bonds:	4
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.566
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.95
MDCK Permeability:	2.770208811853081e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.422

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194
Plasma Protein Binding (PPB):	92.65316009521484%
Volume Distribution (VD):	0.577
Pgp-substrate:	5.225243091583252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.397
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.329
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.53
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.202
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	3.34
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.11
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC79402

Natural Product ID:	NPC79402
*Common Name:**	Ancistrotectorine
IUPAC Name:	2-[(1R,3S)-6,8-dimethoxy-1,2,3-trimethyl-3,4-dihydro-1H-isoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol
Synonyms:	Ancistrotectorine
Standard InCHIKey:	BHQAJMGEYYHIGV-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C26H31NO4/c1-14-11-17-9-8-10-19(29-5)23(17)25(28)21(14)24-20(30-6)13-18-12-15(2)27(4)16(3)22(18)26(24)31-7/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m0/s1
SMILES:	Cc1cc2cccc(c2c(c1c1c(cc2C[C@H](C)N(C)[C@H](C)c2c1OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463908
PubChem CID:	179169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO2073	Ancistrocladus korupensis	Species	Ancistrocladaceae	Eukaryota	n.a.	Cameroon	n.a.	PMID[11430019]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165131]
NPO2073	Ancistrocladus korupensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO2073	Ancistrocladus korupensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249970]
NPO2073	Ancistrocladus korupensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9873424]
NPO2073	Ancistrocladus korupensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	4
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	19.9	ug.mL-1	PMID[538685]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.7	ug.mL-1	PMID[538685]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9.1	ug.mL-1	PMID[538685]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	4.3	ug.mL-1	PMID[538685]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	4.3	ug.mL-1	PMID[538685]

☑ 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 NPC79402 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	324
0.1-0.2	1529
0.2-0.3	6809
0.3-0.4	11190
0.4-0.5	4879
0.5-0.6	9434
0.6-0.7	7114
0.7-0.8	1124
0.8-0.85	210
0.85-0.9	46
0.9-0.95	21
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80759
0.9933	High Similarity	NPC230956
0.9933	High Similarity	NPC119649
0.9933	High Similarity	NPC271388
0.9933	High Similarity	NPC235143
0.9933	High Similarity	NPC205255
0.9867	High Similarity	NPC221864
0.9548	High Similarity	NPC56887
0.9548	High Similarity	NPC193853
0.9548	High Similarity	NPC223077
0.9536	High Similarity	NPC123323
0.9484	High Similarity	NPC209377
0.9299	High Similarity	NPC195392
0.9226	High Similarity	NPC7393
0.9161	High Similarity	NPC79328
0.9097	High Similarity	NPC29647
0.897	High Similarity	NPC257269
0.897	High Similarity	NPC230276
0.8951	High Similarity	NPC239775
0.8909	High Similarity	NPC119068
0.8909	High Similarity	NPC40496
0.8889	High Similarity	NPC118274
0.8889	High Similarity	NPC168753
0.8868	High Similarity	NPC60186
0.882	High Similarity	NPC264850
0.882	High Similarity	NPC13916
0.8812	High Similarity	NPC1229
0.881	High Similarity	NPC16357
0.881	High Similarity	NPC302245
0.881	High Similarity	NPC95426
0.8765	High Similarity	NPC145832
0.8765	High Similarity	NPC117188
0.8765	High Similarity	NPC306555
0.8765	High Similarity	NPC205421
0.8765	High Similarity	NPC81218
0.8765	High Similarity	NPC474931
0.8765	High Similarity	NPC158376
0.8765	High Similarity	NPC12053
0.8758	High Similarity	NPC24465
0.8757	High Similarity	NPC139783
0.8757	High Similarity	NPC65312
0.8706	High Similarity	NPC275680
0.8706	High Similarity	NPC22115
0.8683	High Similarity	NPC474507
0.8679	High Similarity	NPC206736
0.8679	High Similarity	NPC195766
0.8663	High Similarity	NPC476565
0.8642	High Similarity	NPC13504
0.8642	High Similarity	NPC96603
0.8642	High Similarity	NPC78222
0.8642	High Similarity	NPC477563
0.8642	High Similarity	NPC136508
0.8642	High Similarity	NPC306843
0.8642	High Similarity	NPC212794
0.8642	High Similarity	NPC196447
0.8642	High Similarity	NPC253043
0.8605	High Similarity	NPC259350
0.8605	High Similarity	NPC223236
0.8598	High Similarity	NPC204908
0.8598	High Similarity	NPC83198
0.858	High Similarity	NPC324144
0.8563	High Similarity	NPC148709
0.8563	High Similarity	NPC476577
0.8563	High Similarity	NPC173416
0.8562	High Similarity	NPC476572
0.8554	High Similarity	NPC190783
0.8554	High Similarity	NPC232386
0.8554	High Similarity	NPC152680
0.8553	High Similarity	NPC244112
0.8506	High Similarity	NPC256124
0.8471	Intermediate Similarity	NPC328155
0.8471	Intermediate Similarity	NPC8836
0.8471	Intermediate Similarity	NPC7715
0.8471	Intermediate Similarity	NPC271013
0.8471	Intermediate Similarity	NPC182052
0.8471	Intermediate Similarity	NPC251735
0.8471	Intermediate Similarity	NPC239824
0.8471	Intermediate Similarity	NPC104196
0.8471	Intermediate Similarity	NPC54654
0.8471	Intermediate Similarity	NPC290582
0.8471	Intermediate Similarity	NPC279228
0.8471	Intermediate Similarity	NPC285931
0.8471	Intermediate Similarity	NPC217748
0.8471	Intermediate Similarity	NPC223690
0.8471	Intermediate Similarity	NPC222661
0.8471	Intermediate Similarity	NPC258657
0.8471	Intermediate Similarity	NPC49075
0.8471	Intermediate Similarity	NPC229373
0.8471	Intermediate Similarity	NPC90998
0.8471	Intermediate Similarity	NPC311973
0.8471	Intermediate Similarity	NPC290005
0.8471	Intermediate Similarity	NPC181796
0.8471	Intermediate Similarity	NPC185639
0.8471	Intermediate Similarity	NPC15414
0.8471	Intermediate Similarity	NPC42663
0.8457	Intermediate Similarity	NPC166014
0.8457	Intermediate Similarity	NPC27410
0.8448	Intermediate Similarity	NPC478093
0.8443	Intermediate Similarity	NPC66341
0.8443	Intermediate Similarity	NPC192135
0.8443	Intermediate Similarity	NPC477020
0.8439	Intermediate Similarity	NPC206900
0.8438	Intermediate Similarity	NPC325871
0.8438	Intermediate Similarity	NPC99659
0.8431	Intermediate Similarity	NPC470925
0.843	Intermediate Similarity	NPC57036
0.843	Intermediate Similarity	NPC116465
0.843	Intermediate Similarity	NPC212237
0.8428	Intermediate Similarity	NPC26601
0.8424	Intermediate Similarity	NPC150879
0.8424	Intermediate Similarity	NPC204947
0.8421	Intermediate Similarity	NPC167116
0.8421	Intermediate Similarity	NPC274716
0.8421	Intermediate Similarity	NPC254441
0.8412	Intermediate Similarity	NPC286119
0.8402	Intermediate Similarity	NPC114364
0.8402	Intermediate Similarity	NPC320223
0.84	Intermediate Similarity	NPC478092
0.84	Intermediate Similarity	NPC478091
0.84	Intermediate Similarity	NPC30182
0.84	Intermediate Similarity	NPC473589
0.8385	Intermediate Similarity	NPC186063
0.8383	Intermediate Similarity	NPC19520
0.8383	Intermediate Similarity	NPC149090
0.8363	Intermediate Similarity	NPC30779
0.8344	Intermediate Similarity	NPC476151
0.8333	Intermediate Similarity	NPC82763
0.8324	Intermediate Similarity	NPC214116
0.8323	Intermediate Similarity	NPC276588
0.8323	Intermediate Similarity	NPC207757
0.8323	Intermediate Similarity	NPC278799
0.8323	Intermediate Similarity	NPC5238
0.8323	Intermediate Similarity	NPC26240
0.8323	Intermediate Similarity	NPC469817
0.8323	Intermediate Similarity	NPC193949
0.8323	Intermediate Similarity	NPC39701
0.8323	Intermediate Similarity	NPC172765
0.8323	Intermediate Similarity	NPC69712
0.8323	Intermediate Similarity	NPC110416
0.8323	Intermediate Similarity	NPC189266
0.8323	Intermediate Similarity	NPC54379
0.8323	Intermediate Similarity	NPC2413
0.8323	Intermediate Similarity	NPC477562
0.8323	Intermediate Similarity	NPC204828
0.8323	Intermediate Similarity	NPC127674
0.8323	Intermediate Similarity	NPC184026
0.8323	Intermediate Similarity	NPC249797
0.8323	Intermediate Similarity	NPC295691
0.8303	Intermediate Similarity	NPC169743
0.8303	Intermediate Similarity	NPC134858
0.8302	Intermediate Similarity	NPC276665
0.8302	Intermediate Similarity	NPC265473
0.8284	Intermediate Similarity	NPC229166
0.8284	Intermediate Similarity	NPC199465
0.8284	Intermediate Similarity	NPC128560
0.8276	Intermediate Similarity	NPC476576
0.8276	Intermediate Similarity	NPC186546
0.8274	Intermediate Similarity	NPC198498
0.8274	Intermediate Similarity	NPC317145
0.8274	Intermediate Similarity	NPC63646
0.8274	Intermediate Similarity	NPC115284
0.8274	Intermediate Similarity	NPC10908
0.8274	Intermediate Similarity	NPC227060
0.8274	Intermediate Similarity	NPC276890
0.8274	Intermediate Similarity	NPC76682
0.8274	Intermediate Similarity	NPC317439
0.825	Intermediate Similarity	NPC81733
0.825	Intermediate Similarity	NPC326316
0.8242	Intermediate Similarity	NPC233650
0.8239	Intermediate Similarity	NPC92541
0.8239	Intermediate Similarity	NPC103379
0.8239	Intermediate Similarity	NPC219162
0.8239	Intermediate Similarity	NPC477565
0.8235	Intermediate Similarity	NPC293093
0.8235	Intermediate Similarity	NPC241704
0.8229	Intermediate Similarity	NPC48490
0.8229	Intermediate Similarity	NPC274661
0.8229	Intermediate Similarity	NPC82457
0.8229	Intermediate Similarity	NPC175890
0.8229	Intermediate Similarity	NPC11296
0.8225	Intermediate Similarity	NPC12424
0.8225	Intermediate Similarity	NPC41376
0.8225	Intermediate Similarity	NPC129518
0.8225	Intermediate Similarity	NPC251580
0.8217	Intermediate Similarity	NPC185838
0.8208	Intermediate Similarity	NPC302275
0.8204	Intermediate Similarity	NPC298979
0.8204	Intermediate Similarity	NPC247389
0.8204	Intermediate Similarity	NPC210140
0.8202	Intermediate Similarity	NPC234318
0.8198	Intermediate Similarity	NPC32413
0.8198	Intermediate Similarity	NPC474506
0.8182	Intermediate Similarity	NPC191132
0.8182	Intermediate Similarity	NPC60295
0.8176	Intermediate Similarity	NPC147390
0.8176	Intermediate Similarity	NPC246587
0.8176	Intermediate Similarity	NPC24233
0.8176	Intermediate Similarity	NPC135538
0.8176	Intermediate Similarity	NPC428
0.8176	Intermediate Similarity	NPC130941

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 NPC79402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	757
0.2-0.3	968
0.3-0.4	1953
0.4-0.5	2594
0.5-0.6	1698
0.6-0.7	820
0.7-0.8	150
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD8453	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD8054	Approved
0.8471	Intermediate Similarity	NPD8053	Approved
0.8274	Intermediate Similarity	NPD8252	Approved
0.8274	Intermediate Similarity	NPD8251	Approved
0.8274	Intermediate Similarity	NPD8099	Discontinued
0.8225	Intermediate Similarity	NPD8156	Discontinued
0.8171	Intermediate Similarity	NPD6788	Approved
0.8113	Intermediate Similarity	NPD4584	Approved
0.805	Intermediate Similarity	NPD2420	Approved
0.805	Intermediate Similarity	NPD2421	Approved
0.8	Intermediate Similarity	NPD7447	Phase 1
0.7962	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7213	Phase 3
0.7937	Intermediate Similarity	NPD7212	Phase 2
0.784	Intermediate Similarity	NPD6090	Discontinued
0.7811	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4474	Approved
0.7792	Intermediate Similarity	NPD4475	Approved
0.7742	Intermediate Similarity	NPD2238	Phase 2
0.7709	Intermediate Similarity	NPD7906	Approved
0.7662	Intermediate Similarity	NPD4625	Phase 3
0.7654	Intermediate Similarity	NPD3845	Phase 1
0.7628	Intermediate Similarity	NPD3110	Approved
0.7628	Intermediate Similarity	NPD3109	Approved
0.7616	Intermediate Similarity	NPD3051	Approved
0.7613	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7598	Phase 2
0.7595	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4055	Discovery
0.7584	Intermediate Similarity	NPD4577	Approved
0.7584	Intermediate Similarity	NPD4578	Approved
0.7572	Intermediate Similarity	NPD2970	Approved
0.7572	Intermediate Similarity	NPD2969	Approved
0.7557	Intermediate Similarity	NPD7479	Phase 2
0.7556	Intermediate Similarity	NPD4663	Approved
0.7547	Intermediate Similarity	NPD1753	Discontinued
0.7529	Intermediate Similarity	NPD27	Approved
0.7529	Intermediate Similarity	NPD2898	Approved
0.7529	Intermediate Similarity	NPD2489	Approved
0.7514	Intermediate Similarity	NPD6747	Phase 1
0.75	Intermediate Similarity	NPD6042	Phase 2
0.75	Intermediate Similarity	NPD3124	Discontinued
0.75	Intermediate Similarity	NPD42	Phase 2
0.75	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7313	Approved
0.7486	Intermediate Similarity	NPD7312	Approved
0.7486	Intermediate Similarity	NPD7310	Approved
0.7486	Intermediate Similarity	NPD7311	Approved
0.7485	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7833	Phase 2
0.7485	Intermediate Similarity	NPD7831	Phase 2
0.7485	Intermediate Similarity	NPD5241	Discontinued
0.7485	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7455	Intermediate Similarity	NPD1424	Approved
0.7444	Intermediate Similarity	NPD7309	Approved
0.7442	Intermediate Similarity	NPD7400	Phase 3
0.7439	Intermediate Similarity	NPD6667	Approved
0.7439	Intermediate Similarity	NPD6666	Approved
0.7436	Intermediate Similarity	NPD5156	Approved
0.7436	Intermediate Similarity	NPD5155	Approved
0.7434	Intermediate Similarity	NPD2233	Approved
0.7434	Intermediate Similarity	NPD2230	Approved
0.7434	Intermediate Similarity	NPD2232	Approved
0.7433	Intermediate Similarity	NPD8095	Phase 1
0.7432	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7466	Approved
0.7423	Intermediate Similarity	NPD6748	Discontinued
0.7414	Intermediate Similarity	NPD4010	Discontinued
0.7414	Intermediate Similarity	NPD6071	Discontinued
0.7407	Intermediate Similarity	NPD7037	Approved
0.7399	Intermediate Similarity	NPD6746	Phase 2
0.7396	Intermediate Similarity	NPD4773	Phase 2
0.7396	Intermediate Similarity	NPD4772	Phase 2
0.7381	Intermediate Similarity	NPD4005	Discontinued
0.7381	Intermediate Similarity	NPD4017	Approved
0.7375	Intermediate Similarity	NPD2200	Suspended
0.7372	Intermediate Similarity	NPD3595	Approved
0.7372	Intermediate Similarity	NPD3594	Approved
0.7372	Intermediate Similarity	NPD2605	Approved
0.7372	Intermediate Similarity	NPD2606	Approved
0.7368	Intermediate Similarity	NPD2563	Approved
0.7368	Intermediate Similarity	NPD2560	Approved
0.7353	Intermediate Similarity	NPD7298	Approved
0.7345	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5709	Phase 3
0.7333	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7124	Phase 2
0.7333	Intermediate Similarity	NPD7549	Discontinued
0.7318	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2568	Approved
0.7312	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3637	Approved
0.7308	Intermediate Similarity	NPD3635	Approved
0.7308	Intermediate Similarity	NPD3636	Approved
0.7301	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4666	Phase 3
0.7285	Intermediate Similarity	NPD4093	Discontinued
0.7273	Intermediate Similarity	NPD3692	Discontinued
0.7273	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1669	Approved
0.7262	Intermediate Similarity	NPD1914	Approved
0.7262	Intermediate Similarity	NPD7427	Discontinued
0.7256	Intermediate Similarity	NPD5177	Phase 3
0.7247	Intermediate Similarity	NPD7177	Discontinued
0.7247	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4721	Approved
0.7239	Intermediate Similarity	NPD4725	Approved
0.7239	Intermediate Similarity	NPD4726	Approved
0.7238	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2667	Approved
0.7237	Intermediate Similarity	NPD2668	Approved
0.7235	Intermediate Similarity	NPD4678	Approved
0.7235	Intermediate Similarity	NPD4675	Approved
0.7232	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4481	Phase 3
0.7222	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5303	Approved
0.7219	Intermediate Similarity	NPD5304	Approved
0.7212	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6020	Phase 2
0.7193	Intermediate Similarity	NPD6072	Discontinued
0.7193	Intermediate Similarity	NPD7438	Suspended
0.7179	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4103	Phase 2
0.7178	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2493	Approved
0.7173	Intermediate Similarity	NPD3450	Approved
0.7173	Intermediate Similarity	NPD2494	Approved
0.7173	Intermediate Similarity	NPD3452	Approved
0.716	Intermediate Similarity	NPD6031	Approved
0.716	Intermediate Similarity	NPD3640	Phase 3
0.716	Intermediate Similarity	NPD6030	Approved
0.716	Intermediate Similarity	NPD3641	Approved
0.716	Intermediate Similarity	NPD3639	Approved
0.7143	Intermediate Similarity	NPD2975	Approved
0.7143	Intermediate Similarity	NPD2973	Approved
0.7143	Intermediate Similarity	NPD2974	Approved
0.7143	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5006	Approved
0.7135	Intermediate Similarity	NPD5005	Approved
0.7134	Intermediate Similarity	NPD6584	Phase 3
0.7134	Intermediate Similarity	NPD7030	Discontinued
0.7125	Intermediate Similarity	NPD7477	Discontinued
0.7115	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5754	Discontinued
0.7104	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5677	Discontinued
0.7099	Intermediate Similarity	NPD4097	Suspended
0.7091	Intermediate Similarity	NPD4257	Approved
0.7091	Intermediate Similarity	NPD4256	Phase 2
0.7086	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4098	Discontinued
0.7068	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5718	Phase 2
0.7063	Intermediate Similarity	NPD7294	Phase 1
0.7062	Intermediate Similarity	NPD4583	Approved
0.7062	Intermediate Similarity	NPD7802	Discontinued
0.7062	Intermediate Similarity	NPD4582	Approved
0.7059	Intermediate Similarity	NPD2488	Approved
0.7059	Intermediate Similarity	NPD4727	Phase 1
0.7059	Intermediate Similarity	NPD2490	Approved
0.7053	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4749	Approved
0.7051	Intermediate Similarity	NPD4659	Approved
0.7048	Intermediate Similarity	NPD3060	Approved
0.7041	Intermediate Similarity	NPD7019	Approved
0.7041	Intermediate Similarity	NPD3158	Phase 1
0.7041	Intermediate Similarity	NPD7020	Approved
0.7041	Intermediate Similarity	NPD3157	Approved
0.7032	Intermediate Similarity	NPD1610	Phase 2
0.7031	Intermediate Similarity	NPD4580	Approved
0.703	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5710	Approved
0.7022	Intermediate Similarity	NPD5711	Approved
0.7013	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4108	Discontinued
0.7011	Intermediate Similarity	NPD4585	Approved
0.701	Intermediate Similarity	NPD4004	Approved
0.701	Intermediate Similarity	NPD4002	Approved
0.7	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5938	Phase 3
0.6994	Remote Similarity	NPD5089	Approved
0.6994	Remote Similarity	NPD5090	Approved
0.6993	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6959	Discontinued

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