NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	390.884
LogP:	3.723
LogD:	3.702
LogS:	-4.49
# Rotatable Bonds:	2
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	5.315
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	3.113992715952918e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.495

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.403
Plasma Protein Binding (PPB):	77.44799041748047%
Volume Distribution (VD):	1.925
Pgp-substrate:	19.719654083251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.542
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	5.108
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.875
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.241
Skin Sensitization:	0.928
Carcinogencity:	0.13
Eye Corrosion:	0.046
Eye Irritation:	0.07
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC477355

Natural Product ID:	NPC477355
*Common Name:**	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-hydroxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] acetate
IUPAC Name:	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-hydroxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] acetate
Synonyms:
Standard InCHIKey:	UYGFMYCDFZUFFD-AHUQOVQWSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-11-9-15-14(20(15,4)5)7-8-21(6)19(27-21)16-17(26-13(3)23)12(2)10-22(16,25)18(11)24/h9,12,14-17,19,25H,7-8,10H2,1-6H3/b11-9+/t12-,14-,15-,16+,17-,19+,21+,22+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@@H]3[C@](O3)(CC[C@H]4[C@@H](C4(C)C)/C=C(/C2=O)\C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56673371
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19036584]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	stems	Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh	2006-AUG	PMID[21534583]
NPO28682	Jatropha multifida	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	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	<	30	%	PMID[21534583]

☑ 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 NPC477355 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	241
0.1-0.2	1671
0.2-0.3	6875
0.3-0.4	14477
0.4-0.5	8578
0.5-0.6	6731
0.6-0.7	3627
0.7-0.8	450
0.8-0.85	25
0.85-0.9	11
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC477356
0.9565	High Similarity	NPC477354
0.9462	High Similarity	NPC87090
0.9271	High Similarity	NPC118405
0.9239	High Similarity	NPC477361
0.9239	High Similarity	NPC202824
0.883	High Similarity	NPC125180
0.8505	High Similarity	NPC475305
0.8426	Intermediate Similarity	NPC475401
0.8381	Intermediate Similarity	NPC475495
0.8349	Intermediate Similarity	NPC477092
0.8333	Intermediate Similarity	NPC235889
0.8302	Intermediate Similarity	NPC477093
0.8302	Intermediate Similarity	NPC475277
0.8302	Intermediate Similarity	NPC473522
0.8252	Intermediate Similarity	NPC181265
0.8247	Intermediate Similarity	NPC109414
0.819	Intermediate Similarity	NPC258543
0.819	Intermediate Similarity	NPC241927
0.8065	Intermediate Similarity	NPC108045
0.8065	Intermediate Similarity	NPC475622
0.8039	Intermediate Similarity	NPC477950
0.8037	Intermediate Similarity	NPC214797
0.8037	Intermediate Similarity	NPC118860
0.8037	Intermediate Similarity	NPC231589
0.802	Intermediate Similarity	NPC222011
0.8	Intermediate Similarity	NPC470192
0.7963	Intermediate Similarity	NPC71348
0.7963	Intermediate Similarity	NPC170487
0.7961	Intermediate Similarity	NPC308351
0.7961	Intermediate Similarity	NPC271266
0.7959	Intermediate Similarity	NPC221282
0.7928	Intermediate Similarity	NPC118638
0.7921	Intermediate Similarity	NPC69385
0.785	Intermediate Similarity	NPC304495
0.7843	Intermediate Similarity	NPC470188
0.783	Intermediate Similarity	NPC44063
0.7798	Intermediate Similarity	NPC221144
0.7798	Intermediate Similarity	NPC475524
0.7798	Intermediate Similarity	NPC100267
0.7789	Intermediate Similarity	NPC475796
0.7788	Intermediate Similarity	NPC78127
0.7788	Intermediate Similarity	NPC105725
0.7788	Intermediate Similarity	NPC471757
0.7788	Intermediate Similarity	NPC15396
0.7757	Intermediate Similarity	NPC470269
0.7748	Intermediate Similarity	NPC270958
0.7748	Intermediate Similarity	NPC298278
0.7736	Intermediate Similarity	NPC470267
0.7732	Intermediate Similarity	NPC471739
0.7732	Intermediate Similarity	NPC197333
0.7727	Intermediate Similarity	NPC202889
0.7723	Intermediate Similarity	NPC163228
0.7706	Intermediate Similarity	NPC43775
0.7692	Intermediate Similarity	NPC237190
0.7692	Intermediate Similarity	NPC226242
0.7685	Intermediate Similarity	NPC474901
0.7685	Intermediate Similarity	NPC2766
0.7685	Intermediate Similarity	NPC475941
0.7677	Intermediate Similarity	NPC477711
0.767	Intermediate Similarity	NPC221615
0.766	Intermediate Similarity	NPC286229
0.7647	Intermediate Similarity	NPC477357
0.7647	Intermediate Similarity	NPC213078
0.7642	Intermediate Similarity	NPC309190
0.7642	Intermediate Similarity	NPC137657
0.7642	Intermediate Similarity	NPC13385
0.7642	Intermediate Similarity	NPC310586
0.7629	Intermediate Similarity	NPC469676
0.7624	Intermediate Similarity	NPC90453
0.7619	Intermediate Similarity	NPC49393
0.7619	Intermediate Similarity	NPC87351
0.7615	Intermediate Similarity	NPC41551
0.7615	Intermediate Similarity	NPC477103
0.7615	Intermediate Similarity	NPC50223
0.7609	Intermediate Similarity	NPC276769
0.7604	Intermediate Similarity	NPC90446
0.7596	Intermediate Similarity	NPC476274
0.7596	Intermediate Similarity	NPC474720
0.7593	Intermediate Similarity	NPC117604
0.7589	Intermediate Similarity	NPC148458
0.7582	Intermediate Similarity	NPC251435
0.7576	Intermediate Similarity	NPC97032
0.7573	Intermediate Similarity	NPC161493
0.757	Intermediate Similarity	NPC291643
0.757	Intermediate Similarity	NPC265127
0.757	Intermediate Similarity	NPC196528
0.757	Intermediate Similarity	NPC54737
0.757	Intermediate Similarity	NPC314244
0.757	Intermediate Similarity	NPC474101
0.7551	Intermediate Similarity	NPC471738
0.7549	Intermediate Similarity	NPC470978
0.7549	Intermediate Similarity	NPC469599
0.7549	Intermediate Similarity	NPC470974
0.7549	Intermediate Similarity	NPC67584
0.7549	Intermediate Similarity	NPC476053
0.7547	Intermediate Similarity	NPC236390
0.7547	Intermediate Similarity	NPC470839
0.7547	Intermediate Similarity	NPC111323
0.7547	Intermediate Similarity	NPC311612
0.7545	Intermediate Similarity	NPC158523
0.7545	Intermediate Similarity	NPC174471
0.7545	Intermediate Similarity	NPC474871
0.7545	Intermediate Similarity	NPC475937
0.7545	Intermediate Similarity	NPC260786
0.7545	Intermediate Similarity	NPC96739
0.7527	Intermediate Similarity	NPC474056
0.7526	Intermediate Similarity	NPC36350
0.7524	Intermediate Similarity	NPC171759
0.7524	Intermediate Similarity	NPC476270
0.7524	Intermediate Similarity	NPC476240
0.7524	Intermediate Similarity	NPC471767
0.7524	Intermediate Similarity	NPC224720
0.7524	Intermediate Similarity	NPC476223
0.7523	Intermediate Similarity	NPC477102
0.7523	Intermediate Similarity	NPC59489
0.7523	Intermediate Similarity	NPC77089
0.7523	Intermediate Similarity	NPC139838
0.7522	Intermediate Similarity	NPC239273
0.7522	Intermediate Similarity	NPC471854
0.7521	Intermediate Similarity	NPC37968
0.75	Intermediate Similarity	NPC475294
0.75	Intermediate Similarity	NPC52609
0.75	Intermediate Similarity	NPC197386
0.75	Intermediate Similarity	NPC2946
0.75	Intermediate Similarity	NPC1761
0.75	Intermediate Similarity	NPC469368
0.7477	Intermediate Similarity	NPC475970
0.7477	Intermediate Similarity	NPC265499
0.7477	Intermediate Similarity	NPC151216
0.7477	Intermediate Similarity	NPC89227
0.7477	Intermediate Similarity	NPC474741
0.7477	Intermediate Similarity	NPC169843
0.7477	Intermediate Similarity	NPC215643
0.7477	Intermediate Similarity	NPC17138
0.7477	Intermediate Similarity	NPC101825
0.7477	Intermediate Similarity	NPC475391
0.7477	Intermediate Similarity	NPC221511
0.7477	Intermediate Similarity	NPC170212
0.7476	Intermediate Similarity	NPC24956
0.7476	Intermediate Similarity	NPC18019
0.7475	Intermediate Similarity	NPC477710
0.7475	Intermediate Similarity	NPC475902
0.7475	Intermediate Similarity	NPC294480
0.7473	Intermediate Similarity	NPC167049
0.7473	Intermediate Similarity	NPC469691
0.7456	Intermediate Similarity	NPC257457
0.7456	Intermediate Similarity	NPC311554
0.7455	Intermediate Similarity	NPC257240
0.7455	Intermediate Similarity	NPC153036
0.7453	Intermediate Similarity	NPC250594
0.7453	Intermediate Similarity	NPC119601
0.7453	Intermediate Similarity	NPC204450
0.7453	Intermediate Similarity	NPC308726
0.7453	Intermediate Similarity	NPC195290
0.7453	Intermediate Similarity	NPC22388
0.7453	Intermediate Similarity	NPC473928
0.7451	Intermediate Similarity	NPC127019
0.7451	Intermediate Similarity	NPC124207
0.7451	Intermediate Similarity	NPC298919
0.7449	Intermediate Similarity	NPC474045
0.7449	Intermediate Similarity	NPC261253
0.7447	Intermediate Similarity	NPC469620
0.7447	Intermediate Similarity	NPC622
0.7447	Intermediate Similarity	NPC469690
0.7447	Intermediate Similarity	NPC276647
0.7447	Intermediate Similarity	NPC471740
0.7431	Intermediate Similarity	NPC211224
0.7429	Intermediate Similarity	NPC280963
0.7429	Intermediate Similarity	NPC144956
0.7429	Intermediate Similarity	NPC241221
0.7429	Intermediate Similarity	NPC186861
0.7429	Intermediate Similarity	NPC112167
0.7426	Intermediate Similarity	NPC155215
0.7426	Intermediate Similarity	NPC154101
0.7426	Intermediate Similarity	NPC219874
0.7423	Intermediate Similarity	NPC165287
0.7417	Intermediate Similarity	NPC477366
0.7414	Intermediate Similarity	NPC310511
0.7411	Intermediate Similarity	NPC101965
0.7411	Intermediate Similarity	NPC474937
0.7411	Intermediate Similarity	NPC71889
0.7411	Intermediate Similarity	NPC194100
0.7411	Intermediate Similarity	NPC101400
0.7407	Intermediate Similarity	NPC223450
0.7407	Intermediate Similarity	NPC473488
0.7407	Intermediate Similarity	NPC243998
0.7407	Intermediate Similarity	NPC475661
0.7407	Intermediate Similarity	NPC190867
0.7404	Intermediate Similarity	NPC169205
0.7404	Intermediate Similarity	NPC108475
0.7404	Intermediate Similarity	NPC470834
0.7404	Intermediate Similarity	NPC477949
0.7404	Intermediate Similarity	NPC213947
0.7404	Intermediate Similarity	NPC170143
0.7404	Intermediate Similarity	NPC18509
0.74	Intermediate Similarity	NPC52198
0.74	Intermediate Similarity	NPC117405
0.74	Intermediate Similarity	NPC474679
0.74	Intermediate Similarity	NPC41217

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 NPC477355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	2315
0.2-0.3	3998
0.3-0.4	1811
0.4-0.5	424
0.5-0.6	181
0.6-0.7	165
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7957	Intermediate Similarity	NPD6435	Approved
0.7925	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.787	Intermediate Similarity	NPD6649	Approved
0.787	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD6373	Approved
0.785	Intermediate Similarity	NPD6372	Approved
0.783	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD7290	Approved
0.7778	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7742	Intermediate Similarity	NPD5368	Approved
0.7723	Intermediate Similarity	NPD5695	Phase 3
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7706	Intermediate Similarity	NPD6617	Approved
0.7706	Intermediate Similarity	NPD6847	Approved
0.7706	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6012	Approved
0.7685	Intermediate Similarity	NPD6013	Approved
0.7685	Intermediate Similarity	NPD6014	Approved
0.767	Intermediate Similarity	NPD5696	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7636	Intermediate Similarity	NPD8297	Approved
0.7636	Intermediate Similarity	NPD6882	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7474	Intermediate Similarity	NPD5369	Approved
0.7455	Intermediate Similarity	NPD6371	Approved
0.7429	Intermediate Similarity	NPD4696	Approved
0.7429	Intermediate Similarity	NPD5286	Approved
0.7429	Intermediate Similarity	NPD5285	Approved
0.7407	Intermediate Similarity	NPD6008	Approved
0.7404	Intermediate Similarity	NPD4755	Approved
0.7387	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7347	Intermediate Similarity	NPD5363	Approved
0.729	Intermediate Similarity	NPD5226	Approved
0.729	Intermediate Similarity	NPD4633	Approved
0.729	Intermediate Similarity	NPD5224	Approved
0.729	Intermediate Similarity	NPD5225	Approved
0.729	Intermediate Similarity	NPD5211	Phase 2
0.7281	Intermediate Similarity	NPD6274	Approved
0.7273	Intermediate Similarity	NPD5786	Approved
0.7264	Intermediate Similarity	NPD4700	Approved
0.7241	Intermediate Similarity	NPD7100	Approved
0.7241	Intermediate Similarity	NPD7101	Approved
0.7228	Intermediate Similarity	NPD6080	Approved
0.7228	Intermediate Similarity	NPD6673	Approved
0.7228	Intermediate Similarity	NPD6904	Approved
0.7228	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD5175	Approved
0.7222	Intermediate Similarity	NPD5174	Approved
0.7212	Intermediate Similarity	NPD4629	Approved
0.7212	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5210	Approved
0.7196	Intermediate Similarity	NPD5223	Approved
0.7188	Intermediate Similarity	NPD4820	Approved
0.7188	Intermediate Similarity	NPD4822	Approved
0.7188	Intermediate Similarity	NPD4819	Approved
0.7188	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4821	Approved
0.7182	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5141	Approved
0.7155	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7129	Intermediate Similarity	NPD5737	Approved
0.7129	Intermediate Similarity	NPD6672	Approved
0.7115	Intermediate Similarity	NPD5282	Discontinued
0.7105	Intermediate Similarity	NPD4632	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7087	Intermediate Similarity	NPD5284	Approved
0.7087	Intermediate Similarity	NPD5281	Approved
0.7087	Intermediate Similarity	NPD6050	Approved
0.7069	Intermediate Similarity	NPD6317	Approved
0.7059	Intermediate Similarity	NPD1695	Approved
0.7041	Intermediate Similarity	NPD4269	Approved
0.7041	Intermediate Similarity	NPD4270	Approved
0.7034	Intermediate Similarity	NPD6319	Approved
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.699	Remote Similarity	NPD5692	Phase 3
0.6979	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4268	Approved
0.6979	Remote Similarity	NPD4271	Approved
0.6975	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6909	Approved
0.6975	Remote Similarity	NPD6908	Approved
0.697	Remote Similarity	NPD7154	Phase 3
0.6964	Remote Similarity	NPD4730	Approved
0.6964	Remote Similarity	NPD4729	Approved
0.6964	Remote Similarity	NPD5128	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6903	Approved
0.6952	Remote Similarity	NPD6001	Approved
0.6942	Remote Similarity	NPD7492	Approved
0.6937	Remote Similarity	NPD4767	Approved
0.6937	Remote Similarity	NPD4768	Approved
0.6931	Remote Similarity	NPD6098	Approved
0.6931	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD7115	Discovery
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6909	Remote Similarity	NPD4754	Approved
0.69	Remote Similarity	NPD4197	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6885	Remote Similarity	NPD6616	Approved
0.6842	Remote Similarity	NPD5249	Phase 3
0.6842	Remote Similarity	NPD5247	Approved
0.6842	Remote Similarity	NPD5251	Approved
0.6842	Remote Similarity	NPD5250	Approved
0.6842	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD5248	Approved
0.6837	Remote Similarity	NPD4252	Approved
0.6833	Remote Similarity	NPD5983	Phase 2
0.6832	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7078	Approved
0.6822	Remote Similarity	NPD4697	Phase 3
0.6822	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5221	Approved
0.6822	Remote Similarity	NPD5222	Approved
0.6783	Remote Similarity	NPD5217	Approved
0.6783	Remote Similarity	NPD5215	Approved
0.6783	Remote Similarity	NPD5216	Approved
0.6777	Remote Similarity	NPD6370	Approved
0.6774	Remote Similarity	NPD7736	Approved
0.6765	Remote Similarity	NPD4694	Approved
0.6765	Remote Similarity	NPD5280	Approved
0.6765	Remote Similarity	NPD5279	Phase 3
0.6762	Remote Similarity	NPD6411	Approved
0.6762	Remote Similarity	NPD6079	Approved
0.6759	Remote Similarity	NPD5959	Approved
0.6759	Remote Similarity	NPD5173	Approved
0.675	Remote Similarity	NPD6059	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6733	Remote Similarity	NPD3666	Approved
0.6733	Remote Similarity	NPD3665	Phase 1
0.6733	Remote Similarity	NPD3133	Approved
0.6731	Remote Similarity	NPD5328	Approved
0.67	Remote Similarity	NPD4221	Approved
0.67	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD4251	Approved
0.6699	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5135	Approved
0.6696	Remote Similarity	NPD5169	Approved
0.6695	Remote Similarity	NPD6868	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD5127	Approved
0.6635	Remote Similarity	NPD5208	Approved
0.6634	Remote Similarity	NPD5332	Approved
0.6634	Remote Similarity	NPD5331	Approved
0.6606	Remote Similarity	NPD7902	Approved
0.6602	Remote Similarity	NPD4249	Approved
0.66	Remote Similarity	NPD4790	Discontinued
0.6579	Remote Similarity	NPD6614	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5654	Approved
0.6571	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD4786	Approved
0.6542	Remote Similarity	NPD5133	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.65	Remote Similarity	NPD4695	Discontinued
0.6481	Remote Similarity	NPD7748	Approved
0.6476	Remote Similarity	NPD4518	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.6471	Remote Similarity	NPD5167	Approved
0.6449	Remote Similarity	NPD8035	Phase 2
0.6449	Remote Similarity	NPD8034	Phase 2
0.6442	Remote Similarity	NPD4693	Phase 3
0.6442	Remote Similarity	NPD4689	Approved
0.6442	Remote Similarity	NPD4138	Approved
0.6442	Remote Similarity	NPD3618	Phase 1
0.6442	Remote Similarity	NPD4688	Approved
0.6442	Remote Similarity	NPD5205	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