NPASS Compound

Structure

NPC470309 OpenBabel07101718182D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.9836 1.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 2.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.2091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4013 2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 -2.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3559 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2219 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1701 -0.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 2 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 25 1 0 0 0 0 10 11 2 0 0 0 0 10 23 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 3 1 1 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 31 1 1 0 0 0 22 29 1 6 0 0 0 23 33 2 0 0 0 0 24 14 1 6 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 28 1 1 0 0 0 25 30 1 0 0 0 0 26 27 1 6 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 13 1 1 0 0 0 31 34 1 0 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.34
Volume:	520.645
LogP:	4.379
LogD:	3.624
LogS:	-5.101
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	6.442
Fsp3:	0.839
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:	-5.074
MDCK Permeability:	1.8678061678656377e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.582

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	92.45378875732422%
Volume Distribution (VD):	2.309
Pgp-substrate:	4.702878475189209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.96
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	12.026
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.894
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.329
Carcinogencity:	0.828
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC470309

Natural Product ID:	NPC470309
*Common Name:**	SAOBYZGYGWWLDV-PYAUHCBKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SAOBYZGYGWWLDV-PYAUHCBKSA-N
Standard InCHI:	InChI=1S/C31H46O4/c1-17(15-32)18(2)20(4)31(34)21(5)26-24(35-31)14-28(7)25-9-8-22-19(3)23(33)10-11-29(22)16-30(25,29)13-12-27(26,28)6/h10-11,17,19-22,24-26,32,34H,2,8-9,12-16H2,1,3-7H3/t17-,19-,20?,21-,22-,24-,25-,26-,27+,28-,29+,30-,31?/m0/s1
SMILES:	OC[C@@H](C(=C)C(C1(O)O[C@@H]2[C@H]([C@@H]1C)[C@@]1([C@](C2)(C)[C@@H]2CC[C@@H]3[C@@]4([C@@]2(CC1)C4)C=CC(=O)[C@H]3C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951406
PubChem CID:	57393563
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	2.6	n.a.	PMID[545502]
NPT2	Others	Unspecified	FC	=	1.0	n.a.	PMID[545502]
NPT2	Others	Unspecified	FC	=	0.9	n.a.	PMID[545502]

☑ 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 NPC470309 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	210
0.1-0.2	1268
0.2-0.3	5087
0.3-0.4	12124
0.4-0.5	9306
0.5-0.6	6536
0.6-0.7	6548
0.7-0.8	1551
0.8-0.85	55
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8774	High Similarity	NPC214797
0.8774	High Similarity	NPC118860
0.8774	High Similarity	NPC231589
0.8762	High Similarity	NPC241927
0.8762	High Similarity	NPC258543
0.8738	High Similarity	NPC235889
0.8704	High Similarity	NPC471398
0.87	High Similarity	NPC187159
0.8692	High Similarity	NPC170487
0.8679	High Similarity	NPC163314
0.8654	High Similarity	NPC181265
0.8519	High Similarity	NPC71348
0.8505	High Similarity	NPC197428
0.8476	Intermediate Similarity	NPC96377
0.8462	Intermediate Similarity	NPC140723
0.8455	Intermediate Similarity	NPC270958
0.844	Intermediate Similarity	NPC178981
0.84	Intermediate Similarity	NPC111015
0.8381	Intermediate Similarity	NPC121566
0.8381	Intermediate Similarity	NPC255309
0.8381	Intermediate Similarity	NPC100955
0.8365	Intermediate Similarity	NPC22388
0.8333	Intermediate Similarity	NPC108078
0.8318	Intermediate Similarity	NPC470269
0.8304	Intermediate Similarity	NPC118638
0.8302	Intermediate Similarity	NPC63023
0.8302	Intermediate Similarity	NPC95243
0.8288	Intermediate Similarity	NPC302471
0.8273	Intermediate Similarity	NPC202889
0.8273	Intermediate Similarity	NPC471173
0.8273	Intermediate Similarity	NPC477944
0.8273	Intermediate Similarity	NPC471627
0.8241	Intermediate Similarity	NPC246205
0.8208	Intermediate Similarity	NPC164835
0.8208	Intermediate Similarity	NPC228669
0.82	Intermediate Similarity	NPC154101
0.819	Intermediate Similarity	NPC271266
0.819	Intermediate Similarity	NPC308351
0.8182	Intermediate Similarity	NPC477943
0.8182	Intermediate Similarity	NPC186688
0.8173	Intermediate Similarity	NPC218383
0.8163	Intermediate Similarity	NPC58063
0.8155	Intermediate Similarity	NPC475894
0.8148	Intermediate Similarity	NPC469844
0.8148	Intermediate Similarity	NPC61411
0.8142	Intermediate Similarity	NPC475913
0.8137	Intermediate Similarity	NPC469599
0.8131	Intermediate Similarity	NPC278628
0.8131	Intermediate Similarity	NPC231530
0.8119	Intermediate Similarity	NPC470923
0.8119	Intermediate Similarity	NPC242419
0.8119	Intermediate Similarity	NPC235126
0.8113	Intermediate Similarity	NPC221421
0.8108	Intermediate Similarity	NPC260665
0.8108	Intermediate Similarity	NPC52634
0.81	Intermediate Similarity	NPC171441
0.8077	Intermediate Similarity	NPC98868
0.8077	Intermediate Similarity	NPC114274
0.8077	Intermediate Similarity	NPC153792
0.8077	Intermediate Similarity	NPC271387
0.807	Intermediate Similarity	NPC474179
0.807	Intermediate Similarity	NPC161065
0.807	Intermediate Similarity	NPC475834
0.8061	Intermediate Similarity	NPC474778
0.8061	Intermediate Similarity	NPC145879
0.8061	Intermediate Similarity	NPC474733
0.8061	Intermediate Similarity	NPC474732
0.8061	Intermediate Similarity	NPC31564
0.8058	Intermediate Similarity	NPC111684
0.8058	Intermediate Similarity	NPC58052
0.8058	Intermediate Similarity	NPC42042
0.8051	Intermediate Similarity	NPC305496
0.8041	Intermediate Similarity	NPC329043
0.8041	Intermediate Similarity	NPC82902
0.8041	Intermediate Similarity	NPC321187
0.8041	Intermediate Similarity	NPC214043
0.8041	Intermediate Similarity	NPC85774
0.8041	Intermediate Similarity	NPC58841
0.8041	Intermediate Similarity	NPC161423
0.8041	Intermediate Similarity	NPC227064
0.8039	Intermediate Similarity	NPC245972
0.8039	Intermediate Similarity	NPC294266
0.8039	Intermediate Similarity	NPC196485
0.8037	Intermediate Similarity	NPC472228
0.8037	Intermediate Similarity	NPC472227
0.8037	Intermediate Similarity	NPC310586
0.8036	Intermediate Similarity	NPC74727
0.8036	Intermediate Similarity	NPC477580
0.8019	Intermediate Similarity	NPC15396
0.8017	Intermediate Similarity	NPC313528
0.8	Intermediate Similarity	NPC6206
0.8	Intermediate Similarity	NPC31985
0.8	Intermediate Similarity	NPC154072
0.8	Intermediate Similarity	NPC167974
0.8	Intermediate Similarity	NPC83709
0.8	Intermediate Similarity	NPC1015
0.8	Intermediate Similarity	NPC241192
0.7982	Intermediate Similarity	NPC94529
0.7982	Intermediate Similarity	NPC258323
0.7981	Intermediate Similarity	NPC107243
0.7981	Intermediate Similarity	NPC190554
0.7981	Intermediate Similarity	NPC177818
0.7981	Intermediate Similarity	NPC57416
0.798	Intermediate Similarity	NPC475740
0.798	Intermediate Similarity	NPC317590
0.798	Intermediate Similarity	NPC93778
0.7965	Intermediate Similarity	NPC266728
0.7965	Intermediate Similarity	NPC49492
0.7963	Intermediate Similarity	NPC470267
0.7963	Intermediate Similarity	NPC127790
0.7961	Intermediate Similarity	NPC476174
0.7959	Intermediate Similarity	NPC474218
0.7959	Intermediate Similarity	NPC469948
0.7941	Intermediate Similarity	NPC474736
0.7941	Intermediate Similarity	NPC474807
0.7941	Intermediate Similarity	NPC250575
0.7941	Intermediate Similarity	NPC206810
0.7931	Intermediate Similarity	NPC470418
0.7925	Intermediate Similarity	NPC99411
0.7921	Intermediate Similarity	NPC320026
0.7913	Intermediate Similarity	NPC161738
0.7909	Intermediate Similarity	NPC10064
0.7909	Intermediate Similarity	NPC170221
0.7909	Intermediate Similarity	NPC304495
0.7905	Intermediate Similarity	NPC166745
0.7905	Intermediate Similarity	NPC197386
0.7905	Intermediate Similarity	NPC235464
0.7905	Intermediate Similarity	NPC477854
0.79	Intermediate Similarity	NPC328313
0.79	Intermediate Similarity	NPC28227
0.7899	Intermediate Similarity	NPC287423
0.789	Intermediate Similarity	NPC59530
0.789	Intermediate Similarity	NPC44063
0.7885	Intermediate Similarity	NPC322063
0.7879	Intermediate Similarity	NPC195640
0.7879	Intermediate Similarity	NPC118648
0.7879	Intermediate Similarity	NPC222613
0.7879	Intermediate Similarity	NPC475022
0.7879	Intermediate Similarity	NPC469994
0.7876	Intermediate Similarity	NPC326542
0.7876	Intermediate Similarity	NPC165439
0.7876	Intermediate Similarity	NPC474181
0.787	Intermediate Similarity	NPC96268
0.787	Intermediate Similarity	NPC29705
0.787	Intermediate Similarity	NPC222161
0.787	Intermediate Similarity	NPC13149
0.7864	Intermediate Similarity	NPC174051
0.7864	Intermediate Similarity	NPC67831
0.7863	Intermediate Similarity	NPC475431
0.7857	Intermediate Similarity	NPC473246
0.7857	Intermediate Similarity	NPC236217
0.7857	Intermediate Similarity	NPC59453
0.7857	Intermediate Similarity	NPC472265
0.7857	Intermediate Similarity	NPC221758
0.7857	Intermediate Similarity	NPC207251
0.7857	Intermediate Similarity	NPC33913
0.785	Intermediate Similarity	NPC87351
0.7845	Intermediate Similarity	NPC474585
0.7843	Intermediate Similarity	NPC131872
0.7843	Intermediate Similarity	NPC150383
0.7843	Intermediate Similarity	NPC272746
0.7838	Intermediate Similarity	NPC101450
0.7838	Intermediate Similarity	NPC52241
0.7838	Intermediate Similarity	NPC475317
0.7838	Intermediate Similarity	NPC474567
0.7838	Intermediate Similarity	NPC179642
0.7838	Intermediate Similarity	NPC154856
0.7838	Intermediate Similarity	NPC5284
0.7838	Intermediate Similarity	NPC76084
0.7833	Intermediate Similarity	NPC473888
0.783	Intermediate Similarity	NPC474720
0.783	Intermediate Similarity	NPC476303
0.783	Intermediate Similarity	NPC144956
0.783	Intermediate Similarity	NPC15390
0.7822	Intermediate Similarity	NPC76879
0.7822	Intermediate Similarity	NPC268406
0.7822	Intermediate Similarity	NPC2983
0.7822	Intermediate Similarity	NPC326627
0.7822	Intermediate Similarity	NPC26959
0.7822	Intermediate Similarity	NPC310010
0.7822	Intermediate Similarity	NPC54689
0.7818	Intermediate Similarity	NPC469845
0.7818	Intermediate Similarity	NPC472825
0.7818	Intermediate Similarity	NPC295389
0.7815	Intermediate Similarity	NPC47113
0.7815	Intermediate Similarity	NPC174367
0.7815	Intermediate Similarity	NPC93368
0.7807	Intermediate Similarity	NPC190286
0.7807	Intermediate Similarity	NPC148458
0.78	Intermediate Similarity	NPC167877
0.7798	Intermediate Similarity	NPC257353
0.7798	Intermediate Similarity	NPC196528
0.7798	Intermediate Similarity	NPC210178
0.7797	Intermediate Similarity	NPC204812
0.7788	Intermediate Similarity	NPC962
0.7788	Intermediate Similarity	NPC33473
0.7788	Intermediate Similarity	NPC255017
0.7788	Intermediate Similarity	NPC472824
0.7788	Intermediate Similarity	NPC317210
0.7788	Intermediate Similarity	NPC472485

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 NPC470309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1487
0.2-0.3	4045
0.3-0.4	2413
0.4-0.5	536
0.5-0.6	171
0.6-0.7	169
0.7-0.8	142
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8396	Intermediate Similarity	NPD6412	Phase 2
0.8319	Intermediate Similarity	NPD6054	Approved
0.8174	Intermediate Similarity	NPD6370	Approved
0.8131	Intermediate Similarity	NPD6008	Approved
0.8087	Intermediate Similarity	NPD6016	Approved
0.8087	Intermediate Similarity	NPD6015	Approved
0.8041	Intermediate Similarity	NPD3133	Approved
0.8041	Intermediate Similarity	NPD3666	Approved
0.8041	Intermediate Similarity	NPD3665	Phase 1
0.8034	Intermediate Similarity	NPD7492	Approved
0.8018	Intermediate Similarity	NPD6882	Approved
0.8017	Intermediate Similarity	NPD5988	Approved
0.8	Intermediate Similarity	NPD6059	Approved
0.7982	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD6899	Approved
0.7981	Intermediate Similarity	NPD6083	Phase 2
0.7981	Intermediate Similarity	NPD6084	Phase 2
0.7966	Intermediate Similarity	NPD6616	Approved
0.7961	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6399	Phase 3
0.79	Intermediate Similarity	NPD6903	Approved
0.7899	Intermediate Similarity	NPD7078	Approved
0.7895	Intermediate Similarity	NPD6009	Approved
0.789	Intermediate Similarity	NPD5697	Approved
0.7879	Intermediate Similarity	NPD7521	Approved
0.7879	Intermediate Similarity	NPD7334	Approved
0.7879	Intermediate Similarity	NPD6409	Approved
0.7879	Intermediate Similarity	NPD7146	Approved
0.7879	Intermediate Similarity	NPD5330	Approved
0.7879	Intermediate Similarity	NPD6684	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7843	Intermediate Similarity	NPD6079	Approved
0.7838	Intermediate Similarity	NPD7290	Approved
0.7838	Intermediate Similarity	NPD7102	Approved
0.7838	Intermediate Similarity	NPD6883	Approved
0.7833	Intermediate Similarity	NPD7736	Approved
0.783	Intermediate Similarity	NPD4696	Approved
0.783	Intermediate Similarity	NPD5285	Approved
0.783	Intermediate Similarity	NPD5286	Approved
0.7822	Intermediate Similarity	NPD4753	Phase 2
0.7818	Intermediate Similarity	NPD6011	Approved
0.7818	Intermediate Similarity	NPD7320	Approved
0.7798	Intermediate Similarity	NPD6402	Approved
0.7798	Intermediate Similarity	NPD5739	Approved
0.7798	Intermediate Similarity	NPD6675	Approved
0.7798	Intermediate Similarity	NPD7128	Approved
0.7797	Intermediate Similarity	NPD7604	Phase 2
0.7788	Intermediate Similarity	NPD5210	Approved
0.7788	Intermediate Similarity	NPD4629	Approved
0.7788	Intermediate Similarity	NPD4632	Approved
0.7768	Intermediate Similarity	NPD6869	Approved
0.7768	Intermediate Similarity	NPD6847	Approved
0.7768	Intermediate Similarity	NPD6649	Approved
0.7768	Intermediate Similarity	NPD8130	Phase 1
0.7768	Intermediate Similarity	NPD6650	Approved
0.7768	Intermediate Similarity	NPD6617	Approved
0.7767	Intermediate Similarity	NPD4202	Approved
0.7757	Intermediate Similarity	NPD5223	Approved
0.7748	Intermediate Similarity	NPD6012	Approved
0.7748	Intermediate Similarity	NPD6013	Approved
0.7748	Intermediate Similarity	NPD6014	Approved
0.7723	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD8297	Approved
0.7685	Intermediate Similarity	NPD5224	Approved
0.7685	Intermediate Similarity	NPD5225	Approved
0.7685	Intermediate Similarity	NPD5211	Phase 2
0.7685	Intermediate Similarity	NPD4633	Approved
0.7685	Intermediate Similarity	NPD5226	Approved
0.7653	Intermediate Similarity	NPD3667	Approved
0.7653	Intermediate Similarity	NPD4221	Approved
0.7653	Intermediate Similarity	NPD4223	Phase 3
0.7647	Intermediate Similarity	NPD5328	Approved
0.7647	Intermediate Similarity	NPD6067	Discontinued
0.7642	Intermediate Similarity	NPD4755	Approved
0.7619	Intermediate Similarity	NPD5695	Phase 3
0.7615	Intermediate Similarity	NPD5174	Approved
0.7615	Intermediate Similarity	NPD5175	Approved
0.7603	Intermediate Similarity	NPD8293	Discontinued
0.76	Intermediate Similarity	NPD5329	Approved
0.7589	Intermediate Similarity	NPD6373	Approved
0.7589	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD7638	Approved
0.757	Intermediate Similarity	NPD5696	Approved
0.7568	Intermediate Similarity	NPD5701	Approved
0.7561	Intermediate Similarity	NPD5956	Approved
0.7549	Intermediate Similarity	NPD5737	Approved
0.7549	Intermediate Similarity	NPD6672	Approved
0.7547	Intermediate Similarity	NPD5222	Approved
0.7547	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5221	Approved
0.7545	Intermediate Similarity	NPD5141	Approved
0.7542	Intermediate Similarity	NPD6319	Approved
0.7541	Intermediate Similarity	NPD6033	Approved
0.7525	Intermediate Similarity	NPD5690	Phase 2
0.7525	Intermediate Similarity	NPD3618	Phase 1
0.7524	Intermediate Similarity	NPD6001	Approved
0.7522	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7479	Intermediate Similarity	NPD5983	Phase 2
0.7477	Intermediate Similarity	NPD5173	Approved
0.7476	Intermediate Similarity	NPD6080	Approved
0.7476	Intermediate Similarity	NPD6904	Approved
0.7476	Intermediate Similarity	NPD6673	Approved
0.7456	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5207	Approved
0.74	Intermediate Similarity	NPD4788	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7377	Intermediate Similarity	NPD6336	Discontinued
0.7373	Intermediate Similarity	NPD6335	Approved
0.7353	Intermediate Similarity	NPD4688	Approved
0.7353	Intermediate Similarity	NPD4689	Approved
0.7353	Intermediate Similarity	NPD5205	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.7353	Intermediate Similarity	NPD4690	Approved
0.7353	Intermediate Similarity	NPD4693	Phase 3
0.7353	Intermediate Similarity	NPD4138	Approved
0.7347	Intermediate Similarity	NPD4195	Approved
0.7345	Intermediate Similarity	NPD4729	Approved
0.7345	Intermediate Similarity	NPD6686	Approved
0.7345	Intermediate Similarity	NPD4730	Approved
0.7333	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7100	Approved
0.7311	Intermediate Similarity	NPD7101	Approved
0.7297	Intermediate Similarity	NPD4754	Approved
0.7288	Intermediate Similarity	NPD7115	Discovery
0.7288	Intermediate Similarity	NPD6317	Approved
0.7236	Intermediate Similarity	NPD7507	Approved
0.7227	Intermediate Similarity	NPD6313	Approved
0.7227	Intermediate Similarity	NPD6314	Approved
0.7222	Intermediate Similarity	NPD4697	Phase 3
0.7217	Intermediate Similarity	NPD5249	Phase 3
0.7217	Intermediate Similarity	NPD5135	Approved
0.7217	Intermediate Similarity	NPD5248	Approved
0.7217	Intermediate Similarity	NPD5247	Approved
0.7217	Intermediate Similarity	NPD5251	Approved
0.7217	Intermediate Similarity	NPD5250	Approved
0.7217	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5169	Approved
0.7212	Intermediate Similarity	NPD5208	Approved
0.7203	Intermediate Similarity	NPD6274	Approved
0.7196	Intermediate Similarity	NPD7748	Approved
0.7193	Intermediate Similarity	NPD5128	Approved
0.7184	Intermediate Similarity	NPD4694	Approved
0.7184	Intermediate Similarity	NPD6098	Approved
0.7184	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5280	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5693	Phase 1
0.717	Intermediate Similarity	NPD5694	Approved
0.7168	Intermediate Similarity	NPD4767	Approved
0.7168	Intermediate Similarity	NPD4768	Approved
0.7157	Intermediate Similarity	NPD3668	Phase 3
0.7156	Intermediate Similarity	NPD7902	Approved
0.7155	Intermediate Similarity	NPD5217	Approved
0.7155	Intermediate Similarity	NPD5216	Approved
0.7155	Intermediate Similarity	NPD5215	Approved
0.7155	Intermediate Similarity	NPD5127	Approved
0.71	Intermediate Similarity	NPD4695	Discontinued
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7063	Intermediate Similarity	NPD7319	Approved
0.7059	Intermediate Similarity	NPD6868	Approved
0.7049	Intermediate Similarity	NPD7503	Approved
0.7041	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5282	Discontinued
0.7025	Intermediate Similarity	NPD4522	Approved
0.6991	Remote Similarity	NPD6052	Approved
0.6975	Remote Similarity	NPD5167	Approved
0.6944	Remote Similarity	NPD5133	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6939	Remote Similarity	NPD7339	Approved
0.6939	Remote Similarity	NPD6942	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6916	Remote Similarity	NPD5785	Approved
0.6911	Remote Similarity	NPD6909	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD6908	Approved
0.6903	Remote Similarity	NPD7632	Discontinued
0.6903	Remote Similarity	NPD5091	Approved
0.69	Remote Similarity	NPD3617	Approved
0.6897	Remote Similarity	NPD5168	Approved
0.6893	Remote Similarity	NPD5362	Discontinued
0.6887	Remote Similarity	NPD4518	Approved
0.6885	Remote Similarity	NPD7516	Approved
0.6881	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7900	Approved
0.6852	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD8034	Phase 2
0.6852	Remote Similarity	NPD7637	Suspended
0.6847	Remote Similarity	NPD5959	Approved
0.6837	Remote Similarity	NPD4784	Approved
0.6837	Remote Similarity	NPD4785	Approved
0.6829	Remote Similarity	NPD8294	Approved
0.6829	Remote Similarity	NPD8377	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