NPASS Compound

Structure

NPC54803 OpenBabel07101719152D 48 51 0 0 1 0 0 0 0 0999 V2000 6.1545 2.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3717 4.5687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2350 -0.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2169 6.0628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6740 -1.8358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 -0.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 -0.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2325 0.2380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6172 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8715 1.1706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3786 5.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 3.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2446 5.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1106 4.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9631 1.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8492 4.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4845 0.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1232 4.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1548 2.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5660 3.9765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4631 0.2462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9448 5.1006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7840 -0.8419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3786 4.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1106 5.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 0.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3217 0.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8834 1.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5126 3.6963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5922 0.8058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9751 4.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0175 3.0842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3712 1.8999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7090 -0.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8908 1.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 -0.5698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5924 2.5271 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.7825 -0.7868 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 2.1614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8632 2.7598 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 -3.9767 5.6963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5988 5.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9719 3.3828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2327 -1.2624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8813 1.6228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3950 -1.4742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9509 5.2106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 6 41 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 26 2 0 0 0 0 10 28 2 0 0 0 0 11 13 1 0 0 0 0 11 24 2 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 2 1 1 0 0 0 20 32 1 0 0 0 0 21 3 1 6 0 0 0 21 34 1 0 0 0 0 22 4 1 1 0 0 0 22 48 1 0 0 0 0 23 5 1 1 0 0 0 23 36 1 0 0 0 0 23 38 1 0 0 0 0 25 42 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 33 2 0 0 0 0 28 39 1 0 0 0 0 29 24 1 1 0 0 0 29 40 1 0 0 0 0 30 17 1 6 0 0 0 30 35 1 0 0 0 0 30 41 1 0 0 0 0 31 43 2 0 0 0 0 31 48 1 0 0 0 0 32 44 1 1 0 0 0 33 37 1 0 0 0 0 33 39 1 0 0 0 0 34 38 2 3 0 0 0 34 45 1 0 0 0 0 35 40 2 3 0 0 0 35 46 1 0 0 0 0 36 41 1 0 0 0 0 36 47 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	724.25
Volume:	690.151
LogP:	4.258
LogD:	3.951
LogS:	-4.228
# Rotatable Bonds:	3
TPSA:	161.06
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.194
Synthetic Accessibility Score:	5.396
Fsp3:	0.444
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:	-5.264
MDCK Permeability:	1.0299167115590535e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	94.17071533203125%
Volume Distribution (VD):	0.492
Pgp-substrate:	4.205225944519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.467
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	3.549
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.089
Carcinogencity:	0.437
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.187

Download Data

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

Natural Product: NPC54803

Natural Product ID:	NPC54803
*Common Name:**	Jasplakinolide Ca
IUPAC Name:	(4R,7R,10S,13S,16R,17R,19S)-7-[(2-bromo-1H-indol-3-yl)methyl]-16-hydroxy-4-(4-hydroxyphenyl)-8,10,13,17,19-pentamethyl-15-methylidene-1-oxa-5,8,11-triazacyclononadecane-2,6,9,12-tetrone
Synonyms:	Jasplakinolide Ca
Standard InCHIKey:	BJPMREHPIFRLGM-QKWMIRRZSA-N
Standard InCHI:	InChI=1S/C36H45BrN4O7/c1-19-15-21(3)34(45)38-23(5)36(47)41(6)30(17-27-26-9-7-8-10-28(26)39-33(27)37)35(46)40-29(24-11-13-25(42)14-12-24)18-31(43)48-22(4)16-20(2)32(19)44/h7-14,20-23,29-30,32,39,42,44H,1,15-18H2,2-6H3,(H,38,45)(H,40,46)/t20-,21+,22+,23+,29-,30-,32+/m1/s1
SMILES:	C=C1C[C@H](C)C(=N[C@@H](C)C(=O)N(C)[C@H](Cc2c3ccccc3[nH]c2Br)C(=N[C@H](CC(=O)O[C@@H](C)C[C@@H](C)[C@H]1O)c1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165602
PubChem CID:	45103599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO33106	pipestela candelabra	Species	n.a.	n.a.	n.a.	Pacific	n.a.	PMID[22364566]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	80.0	%	PMID[468964]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	0.0	%	PMID[468964]

☑ 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 NPC54803 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	314
0.1-0.2	1585
0.2-0.3	10156
0.3-0.4	9524
0.4-0.5	14868
0.5-0.6	3641
0.6-0.7	2153
0.7-0.8	426
0.8-0.85	6
0.85-0.9	6
0.9-0.95	2
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321592
0.9902	High Similarity	NPC223409
0.9902	High Similarity	NPC95240
0.9854	High Similarity	NPC100547
0.9806	High Similarity	NPC322135
0.9805	High Similarity	NPC118559
0.9805	High Similarity	NPC124920
0.9805	High Similarity	NPC34580
0.9805	High Similarity	NPC261251
0.9805	High Similarity	NPC304307
0.9758	High Similarity	NPC14288
0.9756	High Similarity	NPC214142
0.9571	High Similarity	NPC284888
0.9526	High Similarity	NPC245055
0.9526	High Similarity	NPC33064
0.9393	High Similarity	NPC82472
0.9317	High Similarity	NPC74969
0.9014	High Similarity	NPC24370
0.9014	High Similarity	NPC319232
0.8858	High Similarity	NPC272549
0.8767	High Similarity	NPC323752
0.8767	High Similarity	NPC323198
0.8722	High Similarity	NPC181081
0.8244	Intermediate Similarity	NPC243716
0.8214	Intermediate Similarity	NPC326363
0.807	Intermediate Similarity	NPC325976
0.8017	Intermediate Similarity	NPC314882
0.7956	Intermediate Similarity	NPC125597
0.7928	Intermediate Similarity	NPC303658
0.7925	Intermediate Similarity	NPC306376
0.7919	Intermediate Similarity	NPC330009
0.7902	Intermediate Similarity	NPC473317
0.787	Intermediate Similarity	NPC220852
0.7851	Intermediate Similarity	NPC33949
0.7845	Intermediate Similarity	NPC28945
0.7837	Intermediate Similarity	NPC315467
0.7824	Intermediate Similarity	NPC476098
0.781	Intermediate Similarity	NPC478006
0.7808	Intermediate Similarity	NPC478158
0.7793	Intermediate Similarity	NPC478157
0.7768	Intermediate Similarity	NPC285343
0.7768	Intermediate Similarity	NPC281049
0.7758	Intermediate Similarity	NPC469928
0.775	Intermediate Similarity	NPC153400
0.7735	Intermediate Similarity	NPC470784
0.7733	Intermediate Similarity	NPC478009
0.7702	Intermediate Similarity	NPC475816
0.7696	Intermediate Similarity	NPC194740
0.7652	Intermediate Similarity	NPC314056
0.7649	Intermediate Similarity	NPC321939
0.7642	Intermediate Similarity	NPC21638
0.7639	Intermediate Similarity	NPC473105
0.7623	Intermediate Similarity	NPC75634
0.7617	Intermediate Similarity	NPC184680
0.7617	Intermediate Similarity	NPC184225
0.7617	Intermediate Similarity	NPC276517
0.7615	Intermediate Similarity	NPC476874
0.7597	Intermediate Similarity	NPC474192
0.7597	Intermediate Similarity	NPC475720
0.759	Intermediate Similarity	NPC478010
0.7585	Intermediate Similarity	NPC470785
0.7579	Intermediate Similarity	NPC478011
0.7566	Intermediate Similarity	NPC305984
0.756	Intermediate Similarity	NPC478013
0.7555	Intermediate Similarity	NPC470501
0.7549	Intermediate Similarity	NPC314176
0.7545	Intermediate Similarity	NPC207020
0.7533	Intermediate Similarity	NPC469594
0.7523	Intermediate Similarity	NPC249040
0.7521	Intermediate Similarity	NPC477630
0.7521	Intermediate Similarity	NPC477635
0.7511	Intermediate Similarity	NPC470502
0.75	Intermediate Similarity	NPC315804
0.75	Intermediate Similarity	NPC313804
0.7489	Intermediate Similarity	NPC162860
0.7477	Intermediate Similarity	NPC270918
0.7466	Intermediate Similarity	NPC470500
0.7456	Intermediate Similarity	NPC473041
0.7455	Intermediate Similarity	NPC155143
0.7449	Intermediate Similarity	NPC216369
0.7446	Intermediate Similarity	NPC64216
0.7446	Intermediate Similarity	NPC470503
0.7445	Intermediate Similarity	NPC152768
0.7445	Intermediate Similarity	NPC322064
0.7445	Intermediate Similarity	NPC148183
0.7444	Intermediate Similarity	NPC39679
0.7443	Intermediate Similarity	NPC315491
0.7443	Intermediate Similarity	NPC45459
0.7441	Intermediate Similarity	NPC478012
0.7434	Intermediate Similarity	NPC54744
0.7434	Intermediate Similarity	NPC469592
0.7434	Intermediate Similarity	NPC471080
0.7409	Intermediate Similarity	NPC475506
0.7403	Intermediate Similarity	NPC220851
0.7399	Intermediate Similarity	NPC88008
0.7399	Intermediate Similarity	NPC54420
0.7373	Intermediate Similarity	NPC89987
0.7371	Intermediate Similarity	NPC125181
0.7371	Intermediate Similarity	NPC475271
0.7371	Intermediate Similarity	NPC263117
0.7371	Intermediate Similarity	NPC242872
0.7364	Intermediate Similarity	NPC313985
0.7364	Intermediate Similarity	NPC49196
0.7364	Intermediate Similarity	NPC195461
0.7364	Intermediate Similarity	NPC81654
0.7364	Intermediate Similarity	NPC249150
0.7364	Intermediate Similarity	NPC79129
0.7357	Intermediate Similarity	NPC229348
0.7354	Intermediate Similarity	NPC277350
0.7353	Intermediate Similarity	NPC477549
0.7352	Intermediate Similarity	NPC102008
0.7342	Intermediate Similarity	NPC165599
0.7336	Intermediate Similarity	NPC312645
0.7333	Intermediate Similarity	NPC72980
0.733	Intermediate Similarity	NPC471944
0.7319	Intermediate Similarity	NPC311906
0.7318	Intermediate Similarity	NPC293917
0.7306	Intermediate Similarity	NPC156704
0.7304	Intermediate Similarity	NPC96321
0.7302	Intermediate Similarity	NPC175474
0.7301	Intermediate Similarity	NPC5145
0.7297	Intermediate Similarity	NPC193761
0.7296	Intermediate Similarity	NPC51388
0.7293	Intermediate Similarity	NPC183407
0.7293	Intermediate Similarity	NPC476114
0.7292	Intermediate Similarity	NPC474183
0.729	Intermediate Similarity	NPC94752
0.7284	Intermediate Similarity	NPC60621
0.7277	Intermediate Similarity	NPC186351
0.7276	Intermediate Similarity	NPC473800
0.7273	Intermediate Similarity	NPC473640
0.7273	Intermediate Similarity	NPC52557
0.7273	Intermediate Similarity	NPC52254
0.7273	Intermediate Similarity	NPC50503
0.7269	Intermediate Similarity	NPC87413
0.7269	Intermediate Similarity	NPC23294
0.7257	Intermediate Similarity	NPC474701
0.7257	Intermediate Similarity	NPC223791
0.7257	Intermediate Similarity	NPC107077
0.7253	Intermediate Similarity	NPC478141
0.7252	Intermediate Similarity	NPC477633
0.7251	Intermediate Similarity	NPC219336
0.7249	Intermediate Similarity	NPC50562
0.7249	Intermediate Similarity	NPC118228
0.7249	Intermediate Similarity	NPC477979
0.7246	Intermediate Similarity	NPC471762
0.7244	Intermediate Similarity	NPC244741
0.7244	Intermediate Similarity	NPC53344
0.7243	Intermediate Similarity	NPC94943
0.724	Intermediate Similarity	NPC100321
0.724	Intermediate Similarity	NPC284685
0.7232	Intermediate Similarity	NPC473376
0.7229	Intermediate Similarity	NPC264285
0.7229	Intermediate Similarity	NPC174788
0.7229	Intermediate Similarity	NPC82070
0.7227	Intermediate Similarity	NPC200553
0.7227	Intermediate Similarity	NPC279189
0.7227	Intermediate Similarity	NPC262898
0.7225	Intermediate Similarity	NPC471304
0.7225	Intermediate Similarity	NPC234999
0.7225	Intermediate Similarity	NPC303951
0.7222	Intermediate Similarity	NPC213629
0.7217	Intermediate Similarity	NPC91179
0.7217	Intermediate Similarity	NPC3207
0.7217	Intermediate Similarity	NPC469896
0.7217	Intermediate Similarity	NPC67658
0.7212	Intermediate Similarity	NPC475910
0.7207	Intermediate Similarity	NPC254240
0.7207	Intermediate Similarity	NPC128265
0.7207	Intermediate Similarity	NPC312870
0.7207	Intermediate Similarity	NPC213308
0.7207	Intermediate Similarity	NPC294909
0.7207	Intermediate Similarity	NPC199851
0.7205	Intermediate Similarity	NPC477610
0.7205	Intermediate Similarity	NPC89508
0.7204	Intermediate Similarity	NPC217372
0.7204	Intermediate Similarity	NPC15573
0.7204	Intermediate Similarity	NPC183662
0.7202	Intermediate Similarity	NPC99666
0.7202	Intermediate Similarity	NPC55493
0.72	Intermediate Similarity	NPC475746
0.7196	Intermediate Similarity	NPC190007
0.7193	Intermediate Similarity	NPC320968
0.7184	Intermediate Similarity	NPC469734
0.7182	Intermediate Similarity	NPC179701
0.7181	Intermediate Similarity	NPC476116
0.7178	Intermediate Similarity	NPC15801
0.7177	Intermediate Similarity	NPC189079
0.7167	Intermediate Similarity	NPC472099
0.7167	Intermediate Similarity	NPC182222
0.7167	Intermediate Similarity	NPC97902
0.7162	Intermediate Similarity	NPC475778
0.7162	Intermediate Similarity	NPC241024
0.7156	Intermediate Similarity	NPC473763
0.7156	Intermediate Similarity	NPC117244
0.7155	Intermediate Similarity	NPC63031
0.715	Intermediate Similarity	NPC139291
0.715	Intermediate Similarity	NPC212535
0.715	Intermediate Similarity	NPC472108
0.7149	Intermediate Similarity	NPC243834

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 NPC54803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	520
0.2-0.3	783
0.3-0.4	1393
0.4-0.5	2639
0.5-0.6	2746
0.6-0.7	816
0.7-0.8	67
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
0.8341	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7603	Discontinued
0.7738	Intermediate Similarity	NPD7470	Discontinued
0.7546	Intermediate Similarity	NPD7948	Phase 1
0.7446	Intermediate Similarity	NPD7717	Approved
0.7446	Intermediate Similarity	NPD7716	Approved
0.7443	Intermediate Similarity	NPD484	Approved
0.7439	Intermediate Similarity	NPD8255	Phase 2
0.7418	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5003	Discontinued
0.738	Intermediate Similarity	NPD7878	Phase 2
0.7373	Intermediate Similarity	NPD4885	Approved
0.7364	Intermediate Similarity	NPD4600	Approved
0.7364	Intermediate Similarity	NPD4601	Approved
0.7352	Intermediate Similarity	NPD53	Approved
0.7352	Intermediate Similarity	NPD7777	Approved
0.7352	Intermediate Similarity	NPD7778	Approved
0.7336	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8356	Approved
0.7318	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7944	Discontinued
0.7289	Intermediate Similarity	NPD2916	Discontinued
0.7281	Intermediate Similarity	NPD3243	Approved
0.728	Intermediate Similarity	NPD7853	Phase 2
0.7277	Intermediate Similarity	NPD3003	Approved
0.7277	Intermediate Similarity	NPD8430	Approved
0.7246	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD8322	Phase 2
0.724	Intermediate Similarity	NPD7955	Approved
0.724	Intermediate Similarity	NPD7956	Approved
0.7232	Intermediate Similarity	NPD8272	Phase 2
0.7229	Intermediate Similarity	NPD5632	Approved
0.7229	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD8463	Approved
0.7216	Intermediate Similarity	NPD8364	Approved
0.7216	Intermediate Similarity	NPD8363	Approved
0.7212	Intermediate Similarity	NPD6376	Discontinued
0.7207	Intermediate Similarity	NPD4500	Approved
0.7207	Intermediate Similarity	NPD4501	Approved
0.72	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7957	Phase 1
0.72	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8016	Phase 3
0.7188	Intermediate Similarity	NPD6176	Phase 1
0.7186	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8359	Phase 2
0.7174	Intermediate Similarity	NPD4897	Phase 2
0.7174	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2175	Phase 3
0.7162	Intermediate Similarity	NPD2176	Approved
0.7162	Intermediate Similarity	NPD8093	Discontinued
0.7162	Intermediate Similarity	NPD2177	Approved
0.716	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8115	Approved
0.7156	Intermediate Similarity	NPD8114	Approved
0.7149	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7708	Approved
0.7143	Intermediate Similarity	NPD5612	Discontinued
0.7137	Intermediate Similarity	NPD8459	Approved
0.7137	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8460	Approved
0.7131	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4086	Phase 1
0.7131	Intermediate Similarity	NPD6517	Phase 3
0.7126	Intermediate Similarity	NPD7181	Phase 3
0.7118	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5164	Discontinued
0.7111	Intermediate Similarity	NPD8072	Approved
0.7104	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5512	Phase 3
0.7098	Intermediate Similarity	NPD7803	Approved
0.7098	Intermediate Similarity	NPD7727	Phase 2
0.7098	Intermediate Similarity	NPD7817	Phase 1
0.7097	Intermediate Similarity	NPD2383	Phase 1
0.7097	Intermediate Similarity	NPD5482	Discontinued
0.7093	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6290	Phase 2
0.7087	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7994	Phase 2
0.7054	Intermediate Similarity	NPD7558	Phase 2
0.7054	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7194	Discontinued
0.705	Intermediate Similarity	NPD8427	Approved
0.705	Intermediate Similarity	NPD8466	Approved
0.705	Intermediate Similarity	NPD8429	Approved
0.705	Intermediate Similarity	NPD8467	Approved
0.705	Intermediate Similarity	NPD8465	Approved
0.705	Intermediate Similarity	NPD8428	Approved
0.7049	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5939	Approved
0.7043	Intermediate Similarity	NPD4502	Phase 2
0.7043	Intermediate Similarity	NPD5936	Approved
0.7032	Intermediate Similarity	NPD4499	Approved
0.7032	Intermediate Similarity	NPD2564	Approved
0.7032	Intermediate Similarity	NPD2565	Phase 2
0.7026	Intermediate Similarity	NPD5902	Approved
0.7026	Intermediate Similarity	NPD5903	Approved
0.7018	Intermediate Similarity	NPD7453	Approved
0.7018	Intermediate Similarity	NPD7452	Approved
0.7018	Intermediate Similarity	NPD7222	Phase 2
0.7017	Intermediate Similarity	NPD8289	Discontinued
0.7017	Intermediate Similarity	NPD3263	Phase 3
0.7014	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1768	Approved
0.6992	Remote Similarity	NPD5507	Approved
0.6992	Remote Similarity	NPD6716	Phase 1
0.6992	Remote Similarity	NPD5506	Approved
0.6991	Remote Similarity	NPD2095	Phase 2
0.6991	Remote Similarity	NPD2094	Phase 2
0.6991	Remote Similarity	NPD8073	Approved
0.6991	Remote Similarity	NPD2092	Phase 2
0.6991	Remote Similarity	NPD5596	Phase 2
0.6987	Remote Similarity	NPD5658	Approved
0.6987	Remote Similarity	NPD3259	Approved
0.6984	Remote Similarity	NPD8247	Approved
0.6984	Remote Similarity	NPD8246	Approved
0.6983	Remote Similarity	NPD8094	Discontinued
0.6983	Remote Similarity	NPD7790	Approved
0.6983	Remote Similarity	NPD4373	Phase 2
0.6983	Remote Similarity	NPD7952	Approved
0.6983	Remote Similarity	NPD7950	Approved
0.6983	Remote Similarity	NPD7953	Approved
0.6983	Remote Similarity	NPD7789	Approved
0.6983	Remote Similarity	NPD7951	Approved
0.6983	Remote Similarity	NPD7791	Approved
0.6982	Remote Similarity	NPD4418	Discontinued
0.6979	Remote Similarity	NPD6770	Approved
0.6977	Remote Similarity	NPD5897	Approved
0.6977	Remote Similarity	NPD5899	Approved
0.6977	Remote Similarity	NPD5898	Approved
0.6974	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8106	Phase 2
0.6971	Remote Similarity	NPD7688	Phase 1
0.6971	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6665	Discontinued
0.6964	Remote Similarity	NPD7946	Pre-registration
0.6962	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2096	Phase 2
0.6959	Remote Similarity	NPD2091	Phase 2
0.6953	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7970	Approved
0.6951	Remote Similarity	NPD7576	Discontinued
0.6951	Remote Similarity	NPD7417	Discontinued
0.6948	Remote Similarity	NPD8358	Approved
0.6947	Remote Similarity	NPD4511	Phase 1
0.6947	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7426	Phase 1
0.6944	Remote Similarity	NPD8370	Discontinued
0.6943	Remote Similarity	NPD8425	Approved
0.6943	Remote Similarity	NPD8426	Approved
0.6942	Remote Similarity	NPD7797	Approved
0.6942	Remote Similarity	NPD7796	Approved
0.6941	Remote Similarity	NPD4948	Discontinued
0.694	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3814	Phase 1
0.693	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8098	Approved
0.693	Remote Similarity	NPD5901	Discontinued
0.6929	Remote Similarity	NPD4952	Phase 3
0.692	Remote Similarity	NPD7726	Phase 1
0.6919	Remote Similarity	NPD2844	Phase 3
0.6917	Remote Similarity	NPD7730	Approved
0.6917	Remote Similarity	NPD7731	Approved
0.6909	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8403	Phase 1
0.69	Remote Similarity	NPD7001	Phase 3
0.6898	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6452	Discontinued
0.6889	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7781	Approved
0.6888	Remote Similarity	NPD5559	Phase 2
0.6888	Remote Similarity	NPD7780	Approved
0.6887	Remote Similarity	NPD1325	Approved
0.6887	Remote Similarity	NPD1326	Approved
0.6886	Remote Similarity	NPD6991	Approved
0.6883	Remote Similarity	NPD4520	Approved
0.6878	Remote Similarity	NPD7180	Phase 3
0.6875	Remote Similarity	NPD6550	Discontinued
0.6875	Remote Similarity	NPD7711	Discontinued
0.6869	Remote Similarity	NPD482	Approved
0.6867	Remote Similarity	NPD8097	Phase 3
0.6867	Remote Similarity	NPD8096	Phase 3
0.6864	Remote Similarity	NPD6985	Discontinued
0.6863	Remote Similarity	NPD5050	Approved
0.686	Remote Similarity	NPD7824	Approved
0.686	Remote Similarity	NPD6456	Discontinued
0.6858	Remote Similarity	NPD8396	Approved

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