NPASS Compound

Structure

NPC269267 OpenBabel07101718222D 36 39 0 0 1 0 0 0 0 0999 V2000 -5.1216 -6.6290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8104 -2.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6547 -1.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4050 0.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5362 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6341 -2.4072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4025 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2773 1.8497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9192 -0.6256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6091 -5.7847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5885 -1.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 -1.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9660 -0.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2605 1.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0826 1.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -3.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6091 -2.4072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2302 1.3409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 1.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8104 -1.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9660 -1.0753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5885 -0.1003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8639 0.5521 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2773 -1.0753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6136 0.7577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6091 -4.0959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5873 0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -1.5628 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4329 0.3872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2773 -0.1003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9102 0.3494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5841 -4.0959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1183 1.5244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -4.9403 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 1 10 1 0 0 0 0 2 21 2 0 0 0 0 3 21 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 10 35 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 14 1 6 0 0 0 24 32 1 0 0 0 0 25 29 1 6 0 0 0 25 31 1 0 0 0 0 26 28 1 6 0 0 0 26 36 1 0 0 0 0 27 33 2 0 0 0 0 27 35 1 0 0 0 0 28 34 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 6 0 0 0 32 9 1 1 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.4
Volume:	557.69
LogP:	6.725
LogD:	5.274
LogS:	-5.767
# Rotatable Bonds:	8
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	4.871
Fsp3:	0.906
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.738
MDCK Permeability:	2.2342368538375013e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.112
30% Bioavailability (F30%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.89542388916016%
Volume Distribution (VD):	1.018
Pgp-substrate:	2.479837656021118%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.345
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.559

ADMET: Excretion

Clearance (CL):	5.597
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.806
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.223
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.95
Carcinogencity:	0.057
Eye Corrosion:	0.233
Eye Irritation:	0.076
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC269267

Natural Product ID:	NPC269267
*Common Name:**	Ethyl Shoreate
IUPAC Name:	ethyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	VTOMCWHNRFVAHK-SFPBSPFFSA-N
Standard InCHI:	InChI=1S/C32H54O4/c1-10-35-27(33)16-17-29(6)22(21(2)3)13-19-31(8)25(29)12-11-23-24(14-18-30(23,31)7)32(9)20-15-26(36-32)28(4,5)34/h22-26,34H,2,10-20H2,1,3-9H3/t22-,23+,24-,25+,26+,29-,30+,31+,32-/m0/s1
SMILES:	CCOC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]1[C@]1(C)CC[C@@H](O1)C(O)(C)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109457
PubChem CID:	76332082
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	14900.0	nM	PMID[517474]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	18400.0	nM	PMID[517474]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	12900.0	nM	PMID[517474]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[517474]

☑ 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 NPC269267 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	191
0.1-0.2	1377
0.2-0.3	6068
0.3-0.4	15391
0.4-0.5	5986
0.5-0.6	5610
0.6-0.7	6772
0.7-0.8	1234
0.8-0.85	48
0.85-0.9	12
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC254572
0.988	High Similarity	NPC229407
0.988	High Similarity	NPC250687
0.988	High Similarity	NPC48824
0.9535	High Similarity	NPC471747
0.9294	High Similarity	NPC474174
0.9294	High Similarity	NPC251808
0.8966	High Similarity	NPC255176
0.8929	High Similarity	NPC311642
0.8929	High Similarity	NPC242771
0.8929	High Similarity	NPC100366
0.8929	High Similarity	NPC164289
0.881	High Similarity	NPC232625
0.8706	High Similarity	NPC148740
0.8706	High Similarity	NPC102156
0.869	High Similarity	NPC170038
0.8617	High Similarity	NPC167974
0.8571	High Similarity	NPC118987
0.8523	High Similarity	NPC475007
0.8454	Intermediate Similarity	NPC471293
0.8427	Intermediate Similarity	NPC167877
0.8404	Intermediate Similarity	NPC253586
0.8391	Intermediate Similarity	NPC471037
0.8387	Intermediate Similarity	NPC279974
0.8384	Intermediate Similarity	NPC224414
0.8384	Intermediate Similarity	NPC258323
0.8333	Intermediate Similarity	NPC4309
0.8265	Intermediate Similarity	NPC255309
0.8247	Intermediate Similarity	NPC94919
0.8235	Intermediate Similarity	NPC321690
0.8229	Intermediate Similarity	NPC108371
0.8218	Intermediate Similarity	NPC101450
0.8218	Intermediate Similarity	NPC106760
0.8182	Intermediate Similarity	NPC95243
0.8182	Intermediate Similarity	NPC63023
0.8182	Intermediate Similarity	NPC96377
0.8172	Intermediate Similarity	NPC291373
0.8152	Intermediate Similarity	NPC471896
0.814	Intermediate Similarity	NPC31302
0.814	Intermediate Similarity	NPC245029
0.8137	Intermediate Similarity	NPC272242
0.8125	Intermediate Similarity	NPC119036
0.8118	Intermediate Similarity	NPC66105
0.8111	Intermediate Similarity	NPC472505
0.8111	Intermediate Similarity	NPC80590
0.81	Intermediate Similarity	NPC59530
0.809	Intermediate Similarity	NPC100391
0.8085	Intermediate Similarity	NPC277399
0.8081	Intermediate Similarity	NPC121566
0.8081	Intermediate Similarity	NPC100955
0.8065	Intermediate Similarity	NPC160506
0.8065	Intermediate Similarity	NPC471901
0.8061	Intermediate Similarity	NPC473928
0.8061	Intermediate Similarity	NPC124544
0.8043	Intermediate Similarity	NPC220498
0.8043	Intermediate Similarity	NPC474889
0.8043	Intermediate Similarity	NPC476733
0.8043	Intermediate Similarity	NPC474570
0.8043	Intermediate Similarity	NPC253618
0.8043	Intermediate Similarity	NPC215029
0.8043	Intermediate Similarity	NPC77001
0.8039	Intermediate Similarity	NPC475563
0.8039	Intermediate Similarity	NPC475134
0.8022	Intermediate Similarity	NPC134197
0.8022	Intermediate Similarity	NPC33768
0.802	Intermediate Similarity	NPC255082
0.8	Intermediate Similarity	NPC476601
0.8	Intermediate Similarity	NPC475414
0.8	Intermediate Similarity	NPC472655
0.8	Intermediate Similarity	NPC173172
0.8	Intermediate Similarity	NPC246445
0.8	Intermediate Similarity	NPC98270
0.7981	Intermediate Similarity	NPC102619
0.7979	Intermediate Similarity	NPC473690
0.7979	Intermediate Similarity	NPC471902
0.7979	Intermediate Similarity	NPC470224
0.7979	Intermediate Similarity	NPC475061
0.7979	Intermediate Similarity	NPC287118
0.7978	Intermediate Similarity	NPC268578
0.7978	Intermediate Similarity	NPC245866
0.7978	Intermediate Similarity	NPC217559
0.7978	Intermediate Similarity	NPC292458
0.7961	Intermediate Similarity	NPC475668
0.7961	Intermediate Similarity	NPC473921
0.7961	Intermediate Similarity	NPC475480
0.7957	Intermediate Similarity	NPC289213
0.7957	Intermediate Similarity	NPC111585
0.7957	Intermediate Similarity	NPC148414
0.7957	Intermediate Similarity	NPC175628
0.7955	Intermediate Similarity	NPC190940
0.7955	Intermediate Similarity	NPC327002
0.7941	Intermediate Similarity	NPC170221
0.7941	Intermediate Similarity	NPC472216
0.7941	Intermediate Similarity	NPC5475
0.7941	Intermediate Similarity	NPC284828
0.7941	Intermediate Similarity	NPC10064
0.7941	Intermediate Similarity	NPC173905
0.7938	Intermediate Similarity	NPC472028
0.7935	Intermediate Similarity	NPC183374
0.7935	Intermediate Similarity	NPC211162
0.7921	Intermediate Similarity	NPC475176
0.7921	Intermediate Similarity	NPC287269
0.7921	Intermediate Similarity	NPC255387
0.7921	Intermediate Similarity	NPC131665
0.7917	Intermediate Similarity	NPC256227
0.7917	Intermediate Similarity	NPC42042
0.7912	Intermediate Similarity	NPC12774
0.7912	Intermediate Similarity	NPC92139
0.7912	Intermediate Similarity	NPC70661
0.7912	Intermediate Similarity	NPC2783
0.7907	Intermediate Similarity	NPC238227
0.7895	Intermediate Similarity	NPC67831
0.7895	Intermediate Similarity	NPC47853
0.7895	Intermediate Similarity	NPC174051
0.7889	Intermediate Similarity	NPC97505
0.7889	Intermediate Similarity	NPC263974
0.7889	Intermediate Similarity	NPC475509
0.7872	Intermediate Similarity	NPC262870
0.7872	Intermediate Similarity	NPC150383
0.7872	Intermediate Similarity	NPC475416
0.7872	Intermediate Similarity	NPC26888
0.7872	Intermediate Similarity	NPC219516
0.7872	Intermediate Similarity	NPC189520
0.7865	Intermediate Similarity	NPC286719
0.7865	Intermediate Similarity	NPC477286
0.7864	Intermediate Similarity	NPC5284
0.7864	Intermediate Similarity	NPC6206
0.7857	Intermediate Similarity	NPC94906
0.7857	Intermediate Similarity	NPC477656
0.7857	Intermediate Similarity	NPC477655
0.7849	Intermediate Similarity	NPC116146
0.7849	Intermediate Similarity	NPC24772
0.7843	Intermediate Similarity	NPC472218
0.7843	Intermediate Similarity	NPC88744
0.7843	Intermediate Similarity	NPC295389
0.7843	Intermediate Similarity	NPC472217
0.7843	Intermediate Similarity	NPC472219
0.7841	Intermediate Similarity	NPC206735
0.7841	Intermediate Similarity	NPC472853
0.7835	Intermediate Similarity	NPC469810
0.7835	Intermediate Similarity	NPC475894
0.7826	Intermediate Similarity	NPC269360
0.7826	Intermediate Similarity	NPC264005
0.7826	Intermediate Similarity	NPC128644
0.7826	Intermediate Similarity	NPC90652
0.7812	Intermediate Similarity	NPC30677
0.7812	Intermediate Similarity	NPC98639
0.7812	Intermediate Similarity	NPC37787
0.7812	Intermediate Similarity	NPC469329
0.7812	Intermediate Similarity	NPC473415
0.7812	Intermediate Similarity	NPC470229
0.7812	Intermediate Similarity	NPC180557
0.7802	Intermediate Similarity	NPC470223
0.7802	Intermediate Similarity	NPC294438
0.7802	Intermediate Similarity	NPC201655
0.7802	Intermediate Similarity	NPC264317
0.78	Intermediate Similarity	NPC221421
0.78	Intermediate Similarity	NPC209298
0.78	Intermediate Similarity	NPC474775
0.78	Intermediate Similarity	NPC36688
0.78	Intermediate Similarity	NPC277074
0.78	Intermediate Similarity	NPC140723
0.7791	Intermediate Similarity	NPC20466
0.7789	Intermediate Similarity	NPC244356
0.7789	Intermediate Similarity	NPC224060
0.7778	Intermediate Similarity	NPC75941
0.7778	Intermediate Similarity	NPC239308
0.7778	Intermediate Similarity	NPC477285
0.7778	Intermediate Similarity	NPC289670
0.7778	Intermediate Similarity	NPC252614
0.7778	Intermediate Similarity	NPC111582
0.7778	Intermediate Similarity	NPC170862
0.7767	Intermediate Similarity	NPC240125
0.7767	Intermediate Similarity	NPC473844
0.7767	Intermediate Similarity	NPC91583
0.7767	Intermediate Similarity	NPC51947
0.7767	Intermediate Similarity	NPC218853
0.7766	Intermediate Similarity	NPC473269
0.7755	Intermediate Similarity	NPC473155
0.7755	Intermediate Similarity	NPC271387
0.7755	Intermediate Similarity	NPC153792
0.7753	Intermediate Similarity	NPC223330
0.7753	Intermediate Similarity	NPC209318
0.7742	Intermediate Similarity	NPC474719
0.7742	Intermediate Similarity	NPC183546
0.7742	Intermediate Similarity	NPC470417
0.7742	Intermediate Similarity	NPC16377
0.7742	Intermediate Similarity	NPC28227
0.7732	Intermediate Similarity	NPC200054
0.7732	Intermediate Similarity	NPC29410
0.7732	Intermediate Similarity	NPC322063
0.7732	Intermediate Similarity	NPC329910
0.7732	Intermediate Similarity	NPC327788
0.7727	Intermediate Similarity	NPC192744
0.7727	Intermediate Similarity	NPC327674
0.7727	Intermediate Similarity	NPC471475
0.7723	Intermediate Similarity	NPC85593
0.7723	Intermediate Similarity	NPC301787
0.7723	Intermediate Similarity	NPC328737
0.7723	Intermediate Similarity	NPC31430

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 NPC269267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1927
0.2-0.3	4150
0.3-0.4	1938
0.4-0.5	484
0.5-0.6	188
0.6-0.7	248
0.7-0.8	44
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
0.8065	Intermediate Similarity	NPD8034	Phase 2
0.8065	Intermediate Similarity	NPD8035	Phase 2
0.7802	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7477	Intermediate Similarity	NPD8133	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7416	Intermediate Similarity	NPD6114	Approved
0.7416	Intermediate Similarity	NPD6697	Approved
0.7416	Intermediate Similarity	NPD6115	Approved
0.7416	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD4788	Approved
0.7368	Intermediate Similarity	NPD6903	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7312	Intermediate Similarity	NPD4786	Approved
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD3702	Approved
0.7273	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6412	Phase 2
0.7228	Intermediate Similarity	NPD7638	Approved
0.7228	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7191	Intermediate Similarity	NPD6117	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7748	Approved
0.717	Intermediate Similarity	NPD7320	Approved
0.7159	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6098	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7156	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7113	Intermediate Similarity	NPD6673	Approved
0.7113	Intermediate Similarity	NPD6080	Approved
0.7113	Intermediate Similarity	NPD6904	Approved
0.7111	Intermediate Similarity	NPD6116	Phase 1
0.7097	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD7524	Approved
0.7009	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.6983	Remote Similarity	NPD7492	Approved
0.6972	Remote Similarity	NPD8130	Phase 1
0.697	Remote Similarity	NPD7637	Suspended
0.6964	Remote Similarity	NPD7115	Discovery
0.6961	Remote Similarity	NPD7902	Approved
0.6949	Remote Similarity	NPD7736	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3666	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6939	Remote Similarity	NPD5328	Approved
0.6939	Remote Similarity	NPD4753	Phase 2
0.6932	Remote Similarity	NPD6081	Approved
0.6932	Remote Similarity	NPD5777	Approved
0.693	Remote Similarity	NPD6054	Approved
0.693	Remote Similarity	NPD6319	Approved
0.693	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD7507	Approved
0.6923	Remote Similarity	NPD6616	Approved
0.6916	Remote Similarity	NPD5697	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4223	Phase 3
0.6915	Remote Similarity	NPD4221	Approved
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD5329	Approved
0.6869	Remote Similarity	NPD5207	Approved
0.6864	Remote Similarity	NPD7078	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6852	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6695	Phase 3
0.6837	Remote Similarity	NPD5208	Approved
0.6832	Remote Similarity	NPD6001	Approved
0.6824	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.6813	Remote Similarity	NPD6933	Approved
0.681	Remote Similarity	NPD6370	Approved
0.6804	Remote Similarity	NPD3618	Phase 1
0.68	Remote Similarity	NPD6079	Approved
0.68	Remote Similarity	NPD5693	Phase 1
0.68	Remote Similarity	NPD7515	Phase 2
0.68	Remote Similarity	NPD5281	Approved
0.68	Remote Similarity	NPD5284	Approved
0.68	Remote Similarity	NPD6050	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6014	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6771	Remote Similarity	NPD4197	Approved
0.6771	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6051	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6752	Remote Similarity	NPD7604	Phase 2
0.675	Remote Similarity	NPD7319	Approved
0.6744	Remote Similarity	NPD4224	Phase 2
0.6742	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7750	Discontinued
0.6733	Remote Similarity	NPD4202	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6015	Approved
0.6724	Remote Similarity	NPD5983	Phase 2
0.6724	Remote Similarity	NPD6016	Approved
0.6702	Remote Similarity	NPD7525	Registered
0.67	Remote Similarity	NPD5692	Phase 3
0.6698	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6336	Discontinued
0.6638	Remote Similarity	NPD8377	Approved
0.6638	Remote Similarity	NPD8294	Approved
0.6636	Remote Similarity	NPD6052	Approved
0.6635	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD5694	Approved
0.6633	Remote Similarity	NPD4689	Approved
0.6633	Remote Similarity	NPD4138	Approved
0.6633	Remote Similarity	NPD4693	Phase 3
0.6633	Remote Similarity	NPD4688	Approved
0.6633	Remote Similarity	NPD4690	Approved
0.6633	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD5205	Approved
0.6629	Remote Similarity	NPD4789	Approved
0.6629	Remote Similarity	NPD4245	Approved
0.6629	Remote Similarity	NPD4244	Approved
0.6609	Remote Similarity	NPD7328	Approved
0.6609	Remote Similarity	NPD7327	Approved
0.6607	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6591	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5360	Phase 3
0.6581	Remote Similarity	NPD8033	Approved
0.6581	Remote Similarity	NPD8379	Approved
0.6581	Remote Similarity	NPD8335	Approved
0.6581	Remote Similarity	NPD8378	Approved
0.6581	Remote Similarity	NPD8296	Approved
0.6581	Remote Similarity	NPD8380	Approved
0.6577	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7516	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4697	Phase 3
0.6529	Remote Similarity	NPD6033	Approved
0.6526	Remote Similarity	NPD6931	Approved
0.6526	Remote Similarity	NPD6930	Phase 2
0.6522	Remote Similarity	NPD3703	Phase 2
0.6522	Remote Similarity	NPD7339	Approved
0.6522	Remote Similarity	NPD6942	Approved
0.6517	Remote Similarity	NPD3698	Phase 2
0.6517	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD4700	Approved
0.6509	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD6067	Discontinued
0.6471	Remote Similarity	NPD6411	Approved
0.6466	Remote Similarity	NPD6335	Approved
0.6465	Remote Similarity	NPD5280	Approved
0.6465	Remote Similarity	NPD4694	Approved
0.6465	Remote Similarity	NPD5690	Phase 2
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4692	Approved
0.6458	Remote Similarity	NPD5369	Approved
0.6458	Remote Similarity	NPD4139	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