NPASS Compound

Structure

CID96759 OpenBabel06191715432D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.2344 -2.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0389 -0.1370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6266 0.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7196 0.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2513 -0.8115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7618 -2.5562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8047 -1.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2129 -1.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2932 -1.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 -3.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9499 -1.9725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.1894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4704 0.5154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5385 -2.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2932 -3.0434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6056 -3.0434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6315 -2.0986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4988 0.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6056 -0.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 -0.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8932 -0.3624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3727 -1.0947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7618 -1.5819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3823 -1.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2932 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8648 -0.2896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3443 -1.1675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6056 -2.0690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9499 -0.2168 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7618 -0.6075 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4494 -1.5819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1874 -2.5162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5276 -1.0039 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 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 31 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 1 0 0 0 28 31 1 6 0 0 0 29 7 1 1 0 0 0 29 34 1 0 0 0 0 30 8 1 6 0 0 0 30 34 1 0 0 0 0 31 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.39
Volume:	525.684
LogP:	7.263
LogD:	5.257
LogS:	-6.604
# Rotatable Bonds:	0
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	5.047
Fsp3:	0.968
Lipinski Rule-of-5:	Accepted
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:	-5.121
MDCK Permeability:	2.1389689209172502e-05
Pgp-inhibitor:	0.192
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.454
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	97.43878936767578%
Volume Distribution (VD):	1.348
Pgp-substrate:	3.0009872913360596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.328
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	6.614
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.637
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.851
Carcinogencity:	0.04
Eye Corrosion:	0.559
Eye Irritation:	0.241
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC96759

Natural Product ID:	NPC96759
*Common Name:**	Cupacinoxepin
IUPAC Name:	n.a.
Synonyms:	Cupacinoxepin
Standard InCHIKey:	ZOSNTVJOXIRCCT-ISLDYSMMSA-N
Standard InCHI:	InChI=1S/C31H52O3/c1-25(2)15-10-16-28(6)23-12-11-22-27(5)17-14-24(32)33-26(3,4)21(27)13-18-29(22,7)34-30(23,8)19-20-31(25,28)9/h21-23H,10-20H2,1-9H3/t21-,22+,23+,27-,28+,29+,30+,31-/m0/s1
SMILES:	O=C1CC[C@]2([C@H](C(O1)(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@](O1)(C)CC[C@@]1([C@]2(C)CCCC1(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1775014
PubChem CID:	52951623
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones

*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
NPO31410	Cupania cinerea	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[21438586]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90000.0	nM	PMID[536885]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	8700.0	nM	PMID[536885]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	71600.0	nM	PMID[536885]

☑ 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 NPC96759 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	532
0.1-0.2	4816
0.2-0.3	15330
0.3-0.4	10012
0.4-0.5	6561
0.5-0.6	4541
0.6-0.7	846
0.7-0.8	58
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8169	Intermediate Similarity	NPC84562
0.8133	Intermediate Similarity	NPC55508
0.8082	Intermediate Similarity	NPC178541
0.8056	Intermediate Similarity	NPC41542
0.8028	Intermediate Similarity	NPC230047
0.8028	Intermediate Similarity	NPC19311
0.775	Intermediate Similarity	NPC125366
0.7632	Intermediate Similarity	NPC478227
0.7632	Intermediate Similarity	NPC197701
0.7625	Intermediate Similarity	NPC73013
0.7625	Intermediate Similarity	NPC201276
0.7625	Intermediate Similarity	NPC80891
0.76	Intermediate Similarity	NPC196197
0.7595	Intermediate Similarity	NPC112463
0.759	Intermediate Similarity	NPC471044
0.759	Intermediate Similarity	NPC181871
0.759	Intermediate Similarity	NPC473336
0.759	Intermediate Similarity	NPC219535
0.759	Intermediate Similarity	NPC473299
0.759	Intermediate Similarity	NPC9060
0.759	Intermediate Similarity	NPC237938
0.7532	Intermediate Similarity	NPC109510
0.7531	Intermediate Similarity	NPC134227
0.75	Intermediate Similarity	NPC31031
0.75	Intermediate Similarity	NPC243594
0.75	Intermediate Similarity	NPC171426
0.75	Intermediate Similarity	NPC80089
0.75	Intermediate Similarity	NPC324700
0.75	Intermediate Similarity	NPC34046
0.75	Intermediate Similarity	NPC474572
0.75	Intermediate Similarity	NPC224802
0.7468	Intermediate Similarity	NPC471046
0.7468	Intermediate Similarity	NPC104806
0.7467	Intermediate Similarity	NPC475977
0.7465	Intermediate Similarity	NPC478126
0.7442	Intermediate Similarity	NPC476379
0.7439	Intermediate Similarity	NPC48756
0.7439	Intermediate Similarity	NPC58631
0.7439	Intermediate Similarity	NPC280781
0.7439	Intermediate Similarity	NPC476071
0.7412	Intermediate Similarity	NPC83242
0.7386	Intermediate Similarity	NPC52756
0.7381	Intermediate Similarity	NPC65133
0.7381	Intermediate Similarity	NPC477434
0.7375	Intermediate Similarity	NPC143250
0.7349	Intermediate Similarity	NPC13494
0.7342	Intermediate Similarity	NPC72444
0.7342	Intermediate Similarity	NPC212733
0.7317	Intermediate Similarity	NPC261616
0.7308	Intermediate Similarity	NPC475230
0.7294	Intermediate Similarity	NPC131350
0.7294	Intermediate Similarity	NPC477445
0.725	Intermediate Similarity	NPC4209
0.7241	Intermediate Similarity	NPC131104
0.7241	Intermediate Similarity	NPC3032
0.7241	Intermediate Similarity	NPC473319
0.7237	Intermediate Similarity	NPC281203
0.7237	Intermediate Similarity	NPC469724
0.7237	Intermediate Similarity	NPC100917
0.7237	Intermediate Similarity	NPC31187
0.7229	Intermediate Similarity	NPC271572
0.7229	Intermediate Similarity	NPC20096
0.7229	Intermediate Similarity	NPC328639
0.7229	Intermediate Similarity	NPC329490
0.7229	Intermediate Similarity	NPC48673
0.7229	Intermediate Similarity	NPC474870
0.7215	Intermediate Similarity	NPC280026
0.7215	Intermediate Similarity	NPC74639
0.7215	Intermediate Similarity	NPC167702
0.7209	Intermediate Similarity	NPC477441
0.72	Intermediate Similarity	NPC42060
0.7195	Intermediate Similarity	NPC477287
0.7195	Intermediate Similarity	NPC476176
0.7179	Intermediate Similarity	NPC247195
0.7179	Intermediate Similarity	NPC469940
0.716	Intermediate Similarity	NPC207010
0.716	Intermediate Similarity	NPC143133
0.716	Intermediate Similarity	NPC471151
0.716	Intermediate Similarity	NPC317913
0.716	Intermediate Similarity	NPC212453
0.716	Intermediate Similarity	NPC298168
0.7159	Intermediate Similarity	NPC471459
0.7159	Intermediate Similarity	NPC471043
0.7159	Intermediate Similarity	NPC67653
0.7143	Intermediate Similarity	NPC295788
0.7143	Intermediate Similarity	NPC61107
0.7143	Intermediate Similarity	NPC289486
0.7143	Intermediate Similarity	NPC102156
0.7143	Intermediate Similarity	NPC121121
0.7143	Intermediate Similarity	NPC148740
0.7126	Intermediate Similarity	NPC239938
0.7126	Intermediate Similarity	NPC470920
0.7125	Intermediate Similarity	NPC179858
0.7125	Intermediate Similarity	NPC186851
0.7123	Intermediate Similarity	NPC306750
0.7111	Intermediate Similarity	NPC474379
0.7108	Intermediate Similarity	NPC477851
0.7105	Intermediate Similarity	NPC476928
0.7093	Intermediate Similarity	NPC477205
0.7089	Intermediate Similarity	NPC123122
0.7089	Intermediate Similarity	NPC81759
0.7079	Intermediate Similarity	NPC18536
0.7079	Intermediate Similarity	NPC475211
0.7079	Intermediate Similarity	NPC88337
0.7079	Intermediate Similarity	NPC185529
0.7079	Intermediate Similarity	NPC77756
0.7079	Intermediate Similarity	NPC50443
0.7079	Intermediate Similarity	NPC472146
0.7079	Intermediate Similarity	NPC470114
0.7073	Intermediate Similarity	NPC472608
0.7059	Intermediate Similarity	NPC269684
0.7059	Intermediate Similarity	NPC476721
0.7051	Intermediate Similarity	NPC108131
0.7051	Intermediate Similarity	NPC477929
0.7045	Intermediate Similarity	NPC471221
0.7045	Intermediate Similarity	NPC476435
0.7045	Intermediate Similarity	NPC221993
0.7045	Intermediate Similarity	NPC236459
0.7037	Intermediate Similarity	NPC474020
0.7037	Intermediate Similarity	NPC198473
0.7033	Intermediate Similarity	NPC477495
0.7024	Intermediate Similarity	NPC285480
0.7024	Intermediate Similarity	NPC73515
0.7024	Intermediate Similarity	NPC12933
0.7024	Intermediate Similarity	NPC30443
0.7024	Intermediate Similarity	NPC260977
0.7024	Intermediate Similarity	NPC476494
0.7024	Intermediate Similarity	NPC475743
0.7024	Intermediate Similarity	NPC45256
0.7013	Intermediate Similarity	NPC470956
0.7011	Intermediate Similarity	NPC472272
0.7011	Intermediate Similarity	NPC248216
0.7	Intermediate Similarity	NPC198054
0.7	Intermediate Similarity	NPC475878
0.7	Intermediate Similarity	NPC272359
0.7	Intermediate Similarity	NPC162164
0.7	Intermediate Similarity	NPC470230
0.6988	Remote Similarity	NPC320144
0.6988	Remote Similarity	NPC220379
0.6986	Remote Similarity	NPC204173
0.6977	Remote Similarity	NPC475509
0.6977	Remote Similarity	NPC156981
0.6977	Remote Similarity	NPC319909
0.6974	Remote Similarity	NPC268736
0.6974	Remote Similarity	NPC477931
0.6966	Remote Similarity	NPC477443
0.6966	Remote Similarity	NPC477440
0.6957	Remote Similarity	NPC82633
0.6951	Remote Similarity	NPC477918
0.6951	Remote Similarity	NPC307865
0.6951	Remote Similarity	NPC474404
0.6941	Remote Similarity	NPC476935
0.6941	Remote Similarity	NPC477284
0.6941	Remote Similarity	NPC258153
0.6941	Remote Similarity	NPC476458
0.6923	Remote Similarity	NPC474962
0.6923	Remote Similarity	NPC476189
0.6923	Remote Similarity	NPC319671
0.6923	Remote Similarity	NPC476734
0.6923	Remote Similarity	NPC469941
0.6923	Remote Similarity	NPC252032
0.6915	Remote Similarity	NPC17183
0.6914	Remote Similarity	NPC477934
0.6914	Remote Similarity	NPC159789
0.6905	Remote Similarity	NPC475456
0.6905	Remote Similarity	NPC472853
0.6897	Remote Similarity	NPC62572
0.6897	Remote Similarity	NPC98270
0.6897	Remote Similarity	NPC224345
0.6897	Remote Similarity	NPC476715
0.6889	Remote Similarity	NPC477442
0.6889	Remote Similarity	NPC477444
0.6889	Remote Similarity	NPC477433
0.6883	Remote Similarity	NPC474221
0.6883	Remote Similarity	NPC130459
0.6883	Remote Similarity	NPC478180
0.6882	Remote Similarity	NPC163685
0.6882	Remote Similarity	NPC116683
0.6882	Remote Similarity	NPC235109
0.6875	Remote Similarity	NPC474755
0.6875	Remote Similarity	NPC279241
0.6875	Remote Similarity	NPC477229
0.6875	Remote Similarity	NPC474123
0.6875	Remote Similarity	NPC68426
0.6875	Remote Similarity	NPC232112
0.6875	Remote Similarity	NPC282905
0.6875	Remote Similarity	NPC476718
0.6867	Remote Similarity	NPC26029
0.6867	Remote Similarity	NPC199965
0.6867	Remote Similarity	NPC476732
0.6867	Remote Similarity	NPC471045
0.6867	Remote Similarity	NPC185465
0.6867	Remote Similarity	NPC329117
0.686	Remote Similarity	NPC471037
0.686	Remote Similarity	NPC15091
0.6848	Remote Similarity	NPC224410
0.6848	Remote Similarity	NPC100257
0.6848	Remote Similarity	NPC470424
0.6848	Remote Similarity	NPC47853
0.6842	Remote Similarity	NPC474768

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 NPC96759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	621
0.1-0.2	4279
0.2-0.3	3024
0.3-0.4	762
0.4-0.5	305
0.5-0.6	119
0.6-0.7	29
0.7-0.8	11
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
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.7403	Intermediate Similarity	NPD5777	Approved
0.725	Intermediate Similarity	NPD6117	Approved
0.7237	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5360	Phase 3
0.7215	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4224	Phase 2
0.716	Intermediate Similarity	NPD6116	Phase 1
0.7024	Intermediate Similarity	NPD1780	Approved
0.7024	Intermediate Similarity	NPD1779	Approved
0.6962	Remote Similarity	NPD6081	Approved
0.6914	Remote Similarity	NPD3702	Approved
0.6914	Remote Similarity	NPD3703	Phase 2
0.675	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4758	Discontinued
0.6709	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3573	Approved
0.6517	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3669	Approved
0.6471	Remote Similarity	NPD5364	Discontinued
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD8034	Phase 2
0.642	Remote Similarity	NPD4245	Approved
0.642	Remote Similarity	NPD4244	Approved
0.642	Remote Similarity	NPD4789	Approved
0.6316	Remote Similarity	NPD7748	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD3698	Phase 2
0.6264	Remote Similarity	NPD6098	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.622	Remote Similarity	NPD2687	Approved
0.622	Remote Similarity	NPD2686	Approved
0.622	Remote Similarity	NPD2254	Approved
0.6203	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7639	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7902	Approved
0.6105	Remote Similarity	NPD7515	Phase 2
0.6098	Remote Similarity	NPD3725	Approved
0.6098	Remote Similarity	NPD3726	Approved
0.6092	Remote Similarity	NPD3671	Phase 1
0.6087	Remote Similarity	NPD7334	Approved
0.6087	Remote Similarity	NPD6409	Approved
0.6087	Remote Similarity	NPD5330	Approved
0.6087	Remote Similarity	NPD7521	Approved
0.6087	Remote Similarity	NPD7146	Approved
0.6087	Remote Similarity	NPD6684	Approved
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6058	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7632	Discontinued
0.6019	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD8418	Phase 2
0.5979	Remote Similarity	NPD6001	Approved
0.5962	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6672	Approved
0.5957	Remote Similarity	NPD5737	Approved
0.5957	Remote Similarity	NPD5208	Approved
0.5957	Remote Similarity	NPD6903	Approved
0.5955	Remote Similarity	NPD6928	Phase 2
0.5946	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6399	Phase 3
0.5849	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1810	Approved
0.5814	Remote Similarity	NPD1811	Approved
0.5794	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.578	Remote Similarity	NPD8133	Approved
0.5773	Remote Similarity	NPD5693	Phase 1
0.5773	Remote Similarity	NPD6050	Approved
0.5769	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4788	Approved
0.5735	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.567	Remote Similarity	NPD5692	Phase 3
0.567	Remote Similarity	NPD5207	Approved
0.5652	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4787	Phase 1
0.5644	Remote Similarity	NPD6083	Phase 2
0.5644	Remote Similarity	NPD6084	Phase 2
0.5631	Remote Similarity	NPD1700	Approved
0.5625	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5694	Approved
0.5607	Remote Similarity	NPD6881	Approved
0.5607	Remote Similarity	NPD7320	Approved
0.5607	Remote Similarity	NPD6899	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