NPASS Compound

Structure

NPC170302 OpenBabel07101719252D 52 54 0 0 1 0 0 0 0 0999 V2000 -4.2081 -1.4772 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 -0.0646 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5245 -2.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1644 -1.0614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5027 -2.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1425 -0.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8772 -2.2203 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 -2.5772 0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 2.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0399 3.5982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5682 -3.1714 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 -3.1650 1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2300 -1.6851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8554 -2.0124 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 -7.8117 -1.5966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9209 -2.6362 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 -1.5827 -1.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6646 5.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5662 0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4736 5.7683 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2490 5.5873 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9785 -0.7862 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5608 -0.0817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5901 -3.3793 0.0000 N 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 -0.7691 4.1860 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 0.9364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 -0.9420 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.7898 -1.3887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9428 -2.8441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2737 -2.1009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8917 1.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6045 -1.3578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 15 1 0 0 0 0 3 16 1 0 0 0 0 4 8 1 0 0 0 0 4 22 2 0 0 0 0 5 9 2 0 0 0 0 5 22 1 0 0 0 0 6 10 1 0 0 0 0 6 23 2 0 0 0 0 7 11 2 0 0 0 0 7 23 1 0 0 0 0 8 24 2 0 0 0 0 9 24 1 0 0 0 0 10 25 2 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 33 1 0 0 0 0 16 41 1 0 0 0 0 17 39 1 0 0 0 0 18 40 1 0 0 0 0 19 42 1 0 0 0 0 20 1 1 6 0 0 0 20 27 1 0 0 0 0 20 43 1 0 0 0 0 21 2 1 6 0 0 0 21 28 1 0 0 0 0 21 44 1 0 0 0 0 24 45 1 0 0 0 0 25 46 1 0 0 0 0 26 33 1 6 0 0 0 26 34 1 0 0 0 0 27 39 2 3 0 0 0 27 47 1 0 0 0 0 28 40 2 3 0 0 0 28 48 1 0 0 0 0 29 34 1 0 0 0 0 29 43 2 3 0 0 0 29 49 1 0 0 0 0 30 33 1 0 0 0 0 30 44 1 0 0 0 0 30 50 2 0 0 0 0 31 35 2 0 0 0 0 31 36 1 0 0 0 0 31 41 1 0 0 0 0 32 37 2 0 0 0 0 32 38 1 0 0 0 0 32 42 1 0 0 0 0 33 51 1 6 0 0 0 34 44 1 0 0 0 0 34 52 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	722.35
Volume:	714.33
LogP:	-0.61
LogD:	-0.27
LogS:	-2.372
# Rotatable Bonds:	21
TPSA:	312.99
# H-Bond Aceptor:	18
# H-Bond Donor:	13
# Rings:	3
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.056
Synthetic Accessibility Score:	5.121
Fsp3:	0.412
Lipinski Rule-of-5:	Rejected
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:	-6.571
MDCK Permeability:	3.0520354812324513e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.939
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	56.910037994384766%
Volume Distribution (VD):	0.892
Pgp-substrate:	44.195762634277344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.165
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	1.809
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.236
Maximum Recommended Daily Dose:	0.427
Skin Sensitization:	0.181
Carcinogencity:	0.241
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC170302

Natural Product ID:	NPC170302
*Common Name:**	Anchinopeptolide A
IUPAC Name:	(2S,3R,4S)-3-[2-(diaminomethylideneamino)ethyl]-4-[3-(diaminomethylideneamino)propyl]-2,4-dihydroxy-N,1-bis[(2S)-1-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
Synonyms:
Standard InCHIKey:	HCBLDZZFUFWBIT-NCVYMDLJSA-N
Standard InCHI:	InChI=1S/C34H46N10O8/c1-20(27(47)39-17-12-22-4-8-24(45)9-5-22)43-29(49)34(52)26(14-19-42-32(37)38)33(51,15-3-16-41-31(35)36)30(50)44(34)21(2)28(48)40-18-13-23-6-10-25(46)11-7-23/h4-13,17-18,20-21,26,45-46,51-52H,3,14-16,19H2,1-2H3,(H,39,47)(H,40,48)(H,43,49)(H4,35,36,41)(H4,37,38,42)/b17-12+,18-13+/t20-,21-,26+,33-,34-/m0/s1
SMILES:	C[C@@H](C(=N/C=C/c1ccc(cc1)O)O)N=C([C@]1([C@H](CCNC(=N)N)[C@@](CCCNC(=N)N)(C(=O)N1[C@@H](C)C(=N/C=C/c1ccc(cc1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443365
PubChem CID:	23427641
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO32717	anchinoe tenacior	Species	Hymedesmiidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[7798957]

☑ 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
Others	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6127	Individual Protein	Bradykinin B1 receptor	Homo sapiens	Activity	=	35.0	%	PMID[543424]
NPT2	Others	Unspecified		Activity	=	35.0	%	PMID[543424]

☑ 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 NPC170302 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	249
0.1-0.2	1329
0.2-0.3	8789
0.3-0.4	9091
0.4-0.5	18388
0.5-0.6	4096
0.6-0.7	564
0.7-0.8	175
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475564
1.0	High Similarity	NPC475409
0.9875	High Similarity	NPC473546
0.8353	Intermediate Similarity	NPC280022
0.8314	Intermediate Similarity	NPC475532
0.8266	Intermediate Similarity	NPC165285
0.814	Intermediate Similarity	NPC129486
0.8129	Intermediate Similarity	NPC61004
0.8125	Intermediate Similarity	NPC119652
0.8125	Intermediate Similarity	NPC97526
0.8092	Intermediate Similarity	NPC198254
0.8092	Intermediate Similarity	NPC274198
0.8092	Intermediate Similarity	NPC276506
0.8057	Intermediate Similarity	NPC17698
0.8043	Intermediate Similarity	NPC477638
0.8043	Intermediate Similarity	NPC477632
0.8022	Intermediate Similarity	NPC61332
0.8022	Intermediate Similarity	NPC240130
0.7933	Intermediate Similarity	NPC473404
0.7912	Intermediate Similarity	NPC94862
0.791	Intermediate Similarity	NPC196243
0.7892	Intermediate Similarity	NPC302715
0.7874	Intermediate Similarity	NPC328649
0.7869	Intermediate Similarity	NPC102959
0.7857	Intermediate Similarity	NPC56685
0.7853	Intermediate Similarity	NPC471165
0.7826	Intermediate Similarity	NPC60516
0.7759	Intermediate Similarity	NPC63931
0.7746	Intermediate Similarity	NPC241794
0.7742	Intermediate Similarity	NPC477631
0.7737	Intermediate Similarity	NPC477551
0.773	Intermediate Similarity	NPC477636
0.7717	Intermediate Similarity	NPC96275
0.7713	Intermediate Similarity	NPC329295
0.7709	Intermediate Similarity	NPC50016
0.7688	Intermediate Similarity	NPC475544
0.7688	Intermediate Similarity	NPC469243
0.768	Intermediate Similarity	NPC153554
0.7674	Intermediate Similarity	NPC326349
0.7674	Intermediate Similarity	NPC323336
0.7665	Intermediate Similarity	NPC16188
0.7661	Intermediate Similarity	NPC476268
0.7647	Intermediate Similarity	NPC202198
0.764	Intermediate Similarity	NPC328494
0.7634	Intermediate Similarity	NPC51047
0.7632	Intermediate Similarity	NPC477552
0.7632	Intermediate Similarity	NPC477550
0.763	Intermediate Similarity	NPC244336
0.7619	Intermediate Similarity	NPC477639
0.7598	Intermediate Similarity	NPC248670
0.7593	Intermediate Similarity	NPC267237
0.7586	Intermediate Similarity	NPC114806
0.7584	Intermediate Similarity	NPC475204
0.7584	Intermediate Similarity	NPC475123
0.7576	Intermediate Similarity	NPC476989
0.7558	Intermediate Similarity	NPC473580
0.7557	Intermediate Similarity	NPC223207
0.7556	Intermediate Similarity	NPC26108
0.753	Intermediate Similarity	NPC168861
0.7529	Intermediate Similarity	NPC473491
0.7529	Intermediate Similarity	NPC24617
0.7515	Intermediate Similarity	NPC214988
0.7514	Intermediate Similarity	NPC290755
0.7514	Intermediate Similarity	NPC304074
0.7514	Intermediate Similarity	NPC471771
0.75	Intermediate Similarity	NPC273755
0.7487	Intermediate Similarity	NPC246591
0.7486	Intermediate Similarity	NPC46009
0.7485	Intermediate Similarity	NPC233702
0.7461	Intermediate Similarity	NPC469443
0.7457	Intermediate Similarity	NPC244509
0.7442	Intermediate Similarity	NPC5194
0.7442	Intermediate Similarity	NPC261934
0.7442	Intermediate Similarity	NPC262166
0.7432	Intermediate Similarity	NPC45037
0.743	Intermediate Similarity	NPC66490
0.741	Intermediate Similarity	NPC48202
0.7407	Intermediate Similarity	NPC470728
0.7403	Intermediate Similarity	NPC137627
0.7389	Intermediate Similarity	NPC40234
0.7382	Intermediate Similarity	NPC80514
0.7374	Intermediate Similarity	NPC302597
0.7374	Intermediate Similarity	NPC478005
0.7353	Intermediate Similarity	NPC311658
0.7351	Intermediate Similarity	NPC477637
0.7348	Intermediate Similarity	NPC89831
0.7337	Intermediate Similarity	NPC269750
0.7337	Intermediate Similarity	NPC194671
0.7308	Intermediate Similarity	NPC306804
0.7278	Intermediate Similarity	NPC141957
0.7278	Intermediate Similarity	NPC107938
0.7278	Intermediate Similarity	NPC294516
0.7278	Intermediate Similarity	NPC326241
0.7273	Intermediate Similarity	NPC294951
0.7268	Intermediate Similarity	NPC279871
0.7268	Intermediate Similarity	NPC473354
0.7236	Intermediate Similarity	NPC220060
0.7222	Intermediate Similarity	NPC254700
0.72	Intermediate Similarity	NPC469444
0.7184	Intermediate Similarity	NPC300443
0.7174	Intermediate Similarity	NPC473402
0.7174	Intermediate Similarity	NPC158277
0.7158	Intermediate Similarity	NPC230611
0.715	Intermediate Similarity	NPC478007
0.7135	Intermediate Similarity	NPC62104
0.7135	Intermediate Similarity	NPC1390
0.7094	Intermediate Similarity	NPC469445
0.709	Intermediate Similarity	NPC471048
0.709	Intermediate Similarity	NPC471050
0.709	Intermediate Similarity	NPC471049
0.7083	Intermediate Similarity	NPC163961
0.7083	Intermediate Similarity	NPC473305
0.7081	Intermediate Similarity	NPC136797
0.7081	Intermediate Similarity	NPC478008
0.7081	Intermediate Similarity	NPC155506
0.7081	Intermediate Similarity	NPC159767
0.7081	Intermediate Similarity	NPC476227
0.7074	Intermediate Similarity	NPC476321
0.7065	Intermediate Similarity	NPC194699
0.7065	Intermediate Similarity	NPC219350
0.7053	Intermediate Similarity	NPC299806
0.7048	Intermediate Similarity	NPC326966
0.7041	Intermediate Similarity	NPC313694
0.7041	Intermediate Similarity	NPC242159
0.7037	Intermediate Similarity	NPC471526
0.6995	Remote Similarity	NPC209463
0.6978	Remote Similarity	NPC22883
0.6978	Remote Similarity	NPC210377
0.6978	Remote Similarity	NPC217804
0.6978	Remote Similarity	NPC5719
0.6977	Remote Similarity	NPC328924
0.6965	Remote Similarity	NPC81845
0.694	Remote Similarity	NPC15068
0.6927	Remote Similarity	NPC469442
0.6927	Remote Similarity	NPC277306
0.6923	Remote Similarity	NPC191863
0.6923	Remote Similarity	NPC133470
0.6923	Remote Similarity	NPC289776
0.6919	Remote Similarity	NPC251439
0.6919	Remote Similarity	NPC323662
0.6902	Remote Similarity	NPC63040
0.6889	Remote Similarity	NPC324850
0.6888	Remote Similarity	NPC65714
0.6882	Remote Similarity	NPC64205
0.6878	Remote Similarity	NPC295795
0.6869	Remote Similarity	NPC323244
0.686	Remote Similarity	NPC25539
0.685	Remote Similarity	NPC473450
0.6818	Remote Similarity	NPC473371
0.6789	Remote Similarity	NPC475421
0.6788	Remote Similarity	NPC138083
0.6786	Remote Similarity	NPC473378
0.6786	Remote Similarity	NPC473407
0.6784	Remote Similarity	NPC471592
0.6784	Remote Similarity	NPC109580
0.6776	Remote Similarity	NPC73655
0.676	Remote Similarity	NPC122590
0.6758	Remote Similarity	NPC319320
0.6758	Remote Similarity	NPC287757
0.6735	Remote Similarity	NPC283207
0.6728	Remote Similarity	NPC283760
0.6726	Remote Similarity	NPC325651
0.6725	Remote Similarity	NPC118099
0.6725	Remote Similarity	NPC474787
0.6725	Remote Similarity	NPC151706
0.6725	Remote Similarity	NPC90194
0.6725	Remote Similarity	NPC260045
0.6725	Remote Similarity	NPC293377
0.6725	Remote Similarity	NPC9687
0.6725	Remote Similarity	NPC474811
0.6725	Remote Similarity	NPC79465
0.6725	Remote Similarity	NPC476102
0.6725	Remote Similarity	NPC475318
0.6725	Remote Similarity	NPC49577
0.6725	Remote Similarity	NPC76785
0.6725	Remote Similarity	NPC273907
0.6725	Remote Similarity	NPC474855
0.6725	Remote Similarity	NPC475598
0.672	Remote Similarity	NPC477462
0.6717	Remote Similarity	NPC328763
0.6703	Remote Similarity	NPC472923
0.6703	Remote Similarity	NPC297145
0.6703	Remote Similarity	NPC197743
0.6701	Remote Similarity	NPC235194
0.6684	Remote Similarity	NPC470112
0.6684	Remote Similarity	NPC234069
0.6684	Remote Similarity	NPC186617
0.6684	Remote Similarity	NPC470903
0.6684	Remote Similarity	NPC167763
0.6667	Remote Similarity	NPC39822
0.665	Remote Similarity	NPC64140
0.665	Remote Similarity	NPC174122
0.6649	Remote Similarity	NPC196091
0.6649	Remote Similarity	NPC471568
0.6649	Remote Similarity	NPC473693
0.6649	Remote Similarity	NPC22014
0.6648	Remote Similarity	NPC7817
0.6648	Remote Similarity	NPC475168
0.6647	Remote Similarity	NPC132636
0.6636	Remote Similarity	NPC473317

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 NPC170302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	422
0.2-0.3	727
0.3-0.4	1798
0.4-0.5	3879
0.5-0.6	2001
0.6-0.7	169
0.7-0.8	9
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
0.8235	Intermediate Similarity	NPD8303	Discontinued
0.7751	Intermediate Similarity	NPD7523	Phase 3
0.7556	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7617	Discontinued
0.7529	Intermediate Similarity	NPD8019	Approved
0.7429	Intermediate Similarity	NPD7495	Discontinued
0.7371	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8076	Discontinued
0.7102	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8292	Phase 2
0.6914	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6836	Approved
0.6893	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7303	Discontinued
0.6869	Remote Similarity	NPD7282	Approved
0.686	Remote Similarity	NPD7450	Phase 2
0.6842	Remote Similarity	NPD6901	Phase 3
0.6821	Remote Similarity	NPD7978	Discontinued
0.6798	Remote Similarity	NPD7613	Discontinued
0.6791	Remote Similarity	NPD5137	Approved
0.6786	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4652	Approved
0.6686	Remote Similarity	NPD3136	Phase 2
0.6686	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6835	Approved
0.6684	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1330	Phase 2
0.6647	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8162	Phase 2
0.6618	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8031	Discontinued
0.6613	Remote Similarity	NPD5218	Approved
0.6613	Remote Similarity	NPD5219	Approved
0.6609	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7451	Discontinued
0.6596	Remote Similarity	NPD7485	Phase 3
0.6596	Remote Similarity	NPD7484	Phase 3
0.6591	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7608	Discontinued
0.6546	Remote Similarity	NPD5027	Approved
0.6546	Remote Similarity	NPD5031	Approved
0.6546	Remote Similarity	NPD5029	Approved
0.6533	Remote Similarity	NPD7283	Approved
0.6532	Remote Similarity	NPD8643	Discontinued
0.6531	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2098	Approved
0.6517	Remote Similarity	NPD6676	Phase 2
0.6514	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5032	Approved
0.6512	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5038	Approved
0.6465	Remote Similarity	NPD5037	Approved
0.645	Remote Similarity	NPD3055	Approved
0.645	Remote Similarity	NPD3053	Approved
0.6436	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4955	Approved
0.6429	Remote Similarity	NPD5034	Approved
0.6429	Remote Similarity	NPD4954	Approved
0.6429	Remote Similarity	NPD5026	Approved
0.6429	Remote Similarity	NPD5028	Approved
0.6429	Remote Similarity	NPD36	Approved
0.6419	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5968	Phase 3
0.6417	Remote Similarity	NPD2097	Approved
0.6414	Remote Similarity	NPD5036	Approved
0.6406	Remote Similarity	NPD6796	Discontinued
0.6404	Remote Similarity	NPD6681	Discovery
0.64	Remote Similarity	NPD2568	Approved
0.64	Remote Similarity	NPD8172	Phase 2
0.64	Remote Similarity	NPD5314	Approved
0.64	Remote Similarity	NPD8173	Phase 2
0.6393	Remote Similarity	NPD7131	Phase 3
0.6391	Remote Similarity	NPD5311	Approved
0.6391	Remote Similarity	NPD5310	Approved
0.6391	Remote Similarity	NPD3125	Approved
0.639	Remote Similarity	NPD7565	Approved
0.6379	Remote Similarity	NPD6346	Approved
0.6378	Remote Similarity	NPD5030	Phase 2
0.6369	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2561	Approved
0.6369	Remote Similarity	NPD2562	Approved
0.6364	Remote Similarity	NPD3555	Approved
0.6364	Remote Similarity	NPD3552	Approved
0.6364	Remote Similarity	NPD3554	Approved
0.6364	Remote Similarity	NPD3553	Approved
0.6343	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5035	Approved
0.6294	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8417	Discontinued
0.6286	Remote Similarity	NPD3059	Approved
0.6286	Remote Similarity	NPD3062	Approved
0.6286	Remote Similarity	NPD3061	Approved
0.6286	Remote Similarity	NPD8416	Discontinued
0.6281	Remote Similarity	NPD6557	Phase 2
0.6277	Remote Similarity	NPD7972	Discontinued
0.6276	Remote Similarity	NPD5190	Phase 2
0.6269	Remote Similarity	NPD8025	Phase 2
0.6269	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5303	Approved
0.6265	Remote Similarity	NPD5304	Approved
0.6264	Remote Similarity	NPD4619	Approved
0.6264	Remote Similarity	NPD4621	Approved
0.625	Remote Similarity	NPD2017	Approved
0.625	Remote Similarity	NPD2889	Approved
0.625	Remote Similarity	NPD2888	Approved
0.625	Remote Similarity	NPD2890	Approved
0.6243	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6189	Approved
0.6233	Remote Similarity	NPD6188	Approved
0.6229	Remote Similarity	NPD7086	Phase 2
0.6224	Remote Similarity	NPD4603	Phase 2
0.6224	Remote Similarity	NPD42	Phase 2
0.6224	Remote Similarity	NPD6042	Phase 2
0.622	Remote Similarity	NPD6863	Phase 2
0.6219	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5033	Approved
0.6205	Remote Similarity	NPD5605	Phase 2
0.6196	Remote Similarity	NPD2874	Phase 2
0.6196	Remote Similarity	NPD6419	Discontinued
0.6196	Remote Similarity	NPD3536	Discontinued
0.619	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2458	Approved
0.6188	Remote Similarity	NPD2459	Approved
0.6188	Remote Similarity	NPD2460	Phase 3
0.6186	Remote Similarity	NPD6187	Approved
0.6186	Remote Similarity	NPD7827	Phase 1
0.6184	Remote Similarity	NPD5856	Discontinued
0.6175	Remote Similarity	NPD7554	Discontinued
0.6172	Remote Similarity	NPD6256	Approved
0.6172	Remote Similarity	NPD6255	Approved
0.6172	Remote Similarity	NPD6254	Approved
0.6171	Remote Similarity	NPD601	Approved
0.6171	Remote Similarity	NPD597	Approved
0.6171	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD598	Approved
0.617	Remote Similarity	NPD2469	Approved
0.617	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.617	Remote Similarity	NPD2468	Approved
0.617	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6072	Discontinued
0.6163	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4103	Phase 2
0.6162	Remote Similarity	NPD6297	Approved
0.6162	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2229	Approved
0.6159	Remote Similarity	NPD2228	Approved
0.6159	Remote Similarity	NPD2234	Approved
0.6158	Remote Similarity	NPD5967	Approved
0.6149	Remote Similarity	NPD5263	Approved
0.6146	Remote Similarity	NPD4466	Phase 1
0.6136	Remote Similarity	NPD1132	Approved
0.6136	Remote Similarity	NPD1130	Approved
0.6136	Remote Similarity	NPD1136	Approved
0.6132	Remote Similarity	NPD6807	Phase 3
0.6126	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6253	Approved
0.612	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6851	Approved
0.6119	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6853	Approved
0.6116	Remote Similarity	NPD4086	Phase 1
0.6114	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4173	Approved
0.6111	Remote Similarity	NPD5557	Phase 1
0.6111	Remote Similarity	NPD3879	Approved
0.6111	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4172	Approved
0.6099	Remote Similarity	NPD2209	Approved
0.6099	Remote Similarity	NPD2211	Approved
0.6094	Remote Similarity	NPD8070	Approved
0.6091	Remote Similarity	NPD3909	Discontinued
0.6082	Remote Similarity	NPD3073	Approved
0.6082	Remote Similarity	NPD3286	Discontinued
0.6082	Remote Similarity	NPD3071	Approved
0.6082	Remote Similarity	NPD3072	Approved
0.608	Remote Similarity	NPD5445	Approved
0.6073	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.607	Remote Similarity	NPD7280	Phase 3
0.607	Remote Similarity	NPD7281	Phase 3
0.6067	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5481	Discontinued
0.6066	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD3878	Approved
0.6054	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3589	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