NPASS Compound

Structure

CID263974 OpenBabel06191716062D 24 27 0 0 1 0 0 0 0 0999 V2000 2.0439 -0.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5075 -0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8391 2.0369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9504 2.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0151 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7537 -1.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7538 1.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2613 -0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0152 0.8703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7538 -0.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1891 -0.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7538 -1.3056 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5076 0.8704 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7538 -0.4352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8704 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6836 2.0369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5076 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2614 1.3055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2978 0.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2614 2.7683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5282 2.0369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 4 24 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 6 1 6 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 16 21 1 0 0 0 0 17 21 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.24
Volume:	358.644
LogP:	3.429
LogD:	3.239
LogS:	-4.222
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	5.577
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.728
MDCK Permeability:	2.2836984499008395e-05
Pgp-inhibitor:	0.639
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.267

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.658
Plasma Protein Binding (PPB):	59.13196563720703%
Volume Distribution (VD):	0.957
Pgp-substrate:	30.734607696533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	8.228
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.251
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.89
Carcinogencity:	0.866
Eye Corrosion:	0.567
Eye Irritation:	0.431
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: NPC263974

Natural Product ID:	NPC263974
*Common Name:**	YTLCFXIFEIWKEL-WHCUZVCWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YTLCFXIFEIWKEL-WHCUZVCWSA-N
Standard InCHI:	InChI=1S/C21H32O3/c1-13-14-6-7-16-19(2)9-5-10-20(3,18(23)24-4)15(19)8-11-21(16,12-14)17(13)22/h14-17,22H,1,5-12H2,2-4H3/t14-,15+,16+,17+,19-,20-,21-/m1/s1
SMILES:	COC(=O)[C@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2CC[C@H](C1)C(=C)[C@@H]3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL605767
PubChem CID:	46233456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075788]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO13162	Glycosmis petelotii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24949913]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463095]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13461	Maytenus buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13162	Glycosmis petelotii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26146	Ruilopezia lindenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15995	Moesziomyces rugulosus	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12829	Ocotea acutifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12346	Daphnandra apatela	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9211	Margyricarpus setosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10762	Brasilia sickii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13461	Maytenus buchananii	Species	Celastraceae	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[534474]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	97.0	%	PMID[534475]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5000.0	nM	PMID[534475]

☑ 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 NPC263974 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	168
0.1-0.2	1387
0.2-0.3	6308
0.3-0.4	15733
0.4-0.5	5955
0.5-0.6	6053
0.6-0.7	4872
0.7-0.8	1979
0.8-0.85	196
0.85-0.9	39
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC170985
0.9375	High Similarity	NPC245866
0.9268	High Similarity	NPC472505
0.9157	High Similarity	NPC134197
0.9036	High Similarity	NPC70661
0.9036	High Similarity	NPC80590
0.9012	High Similarity	NPC46881
0.8902	High Similarity	NPC170862
0.8902	High Similarity	NPC472498
0.8902	High Similarity	NPC471037
0.8824	High Similarity	NPC211162
0.8824	High Similarity	NPC16377
0.8824	High Similarity	NPC183374
0.881	High Similarity	NPC12774
0.878	High Similarity	NPC477858
0.878	High Similarity	NPC145143
0.8721	High Similarity	NPC116146
0.8721	High Similarity	NPC24772
0.8706	High Similarity	NPC33768
0.869	High Similarity	NPC294438
0.869	High Similarity	NPC264317
0.8659	High Similarity	NPC474484
0.8659	High Similarity	NPC103754
0.8625	High Similarity	NPC66105
0.859	High Similarity	NPC472506
0.859	High Similarity	NPC244708
0.859	High Similarity	NPC330659
0.859	High Similarity	NPC161187
0.859	High Similarity	NPC279241
0.8588	High Similarity	NPC469994
0.8588	High Similarity	NPC475007
0.8588	High Similarity	NPC2783
0.8571	High Similarity	NPC165064
0.8523	High Similarity	NPC154101
0.85	High Similarity	NPC246445
0.8488	Intermediate Similarity	NPC472497
0.8488	Intermediate Similarity	NPC269360
0.8488	Intermediate Similarity	NPC264005
0.8488	Intermediate Similarity	NPC472495
0.8471	Intermediate Similarity	NPC292553
0.8471	Intermediate Similarity	NPC201655
0.8471	Intermediate Similarity	NPC283733
0.8462	Intermediate Similarity	NPC475894
0.8462	Intermediate Similarity	NPC164045
0.8462	Intermediate Similarity	NPC107243
0.8452	Intermediate Similarity	NPC472740
0.8444	Intermediate Similarity	NPC205173
0.8434	Intermediate Similarity	NPC164210
0.8427	Intermediate Similarity	NPC243866
0.8415	Intermediate Similarity	NPC192744
0.8415	Intermediate Similarity	NPC471475
0.8415	Intermediate Similarity	NPC201459
0.8395	Intermediate Similarity	NPC471035
0.8395	Intermediate Similarity	NPC106078
0.8395	Intermediate Similarity	NPC68828
0.8395	Intermediate Similarity	NPC212661
0.8391	Intermediate Similarity	NPC4309
0.8391	Intermediate Similarity	NPC471900
0.8391	Intermediate Similarity	NPC160304
0.8391	Intermediate Similarity	NPC255176
0.8391	Intermediate Similarity	NPC146937
0.8391	Intermediate Similarity	NPC474719
0.8387	Intermediate Similarity	NPC253886
0.8387	Intermediate Similarity	NPC121218
0.8372	Intermediate Similarity	NPC155011
0.8372	Intermediate Similarity	NPC187545
0.8372	Intermediate Similarity	NPC322159
0.8372	Intermediate Similarity	NPC472738
0.8353	Intermediate Similarity	NPC476038
0.8353	Intermediate Similarity	NPC194937
0.8353	Intermediate Similarity	NPC82902
0.8333	Intermediate Similarity	NPC91369
0.8333	Intermediate Similarity	NPC110780
0.8315	Intermediate Similarity	NPC471747
0.8315	Intermediate Similarity	NPC475416
0.8295	Intermediate Similarity	NPC2983
0.8295	Intermediate Similarity	NPC54689
0.8295	Intermediate Similarity	NPC215029
0.8295	Intermediate Similarity	NPC155479
0.8295	Intermediate Similarity	NPC220498
0.8295	Intermediate Similarity	NPC476733
0.8295	Intermediate Similarity	NPC57954
0.8295	Intermediate Similarity	NPC213832
0.8293	Intermediate Similarity	NPC247783
0.8293	Intermediate Similarity	NPC63020
0.8293	Intermediate Similarity	NPC269543
0.828	Intermediate Similarity	NPC218383
0.8276	Intermediate Similarity	NPC4643
0.8276	Intermediate Similarity	NPC474684
0.8276	Intermediate Similarity	NPC317590
0.8276	Intermediate Similarity	NPC142361
0.8272	Intermediate Similarity	NPC476601
0.8272	Intermediate Similarity	NPC38141
0.8261	Intermediate Similarity	NPC57416
0.8256	Intermediate Similarity	NPC474218
0.8256	Intermediate Similarity	NPC471224
0.8242	Intermediate Similarity	NPC476174
0.8242	Intermediate Similarity	NPC210214
0.8242	Intermediate Similarity	NPC469599
0.8235	Intermediate Similarity	NPC475726
0.8235	Intermediate Similarity	NPC215893
0.8235	Intermediate Similarity	NPC472743
0.8222	Intermediate Similarity	NPC287118
0.8222	Intermediate Similarity	NPC294263
0.8222	Intermediate Similarity	NPC470375
0.8222	Intermediate Similarity	NPC473690
0.8222	Intermediate Similarity	NPC471902
0.8222	Intermediate Similarity	NPC470376
0.8211	Intermediate Similarity	NPC469985
0.8202	Intermediate Similarity	NPC219937
0.8202	Intermediate Similarity	NPC194485
0.8202	Intermediate Similarity	NPC53890
0.8202	Intermediate Similarity	NPC100313
0.8202	Intermediate Similarity	NPC169933
0.8202	Intermediate Similarity	NPC123252
0.8202	Intermediate Similarity	NPC469400
0.8191	Intermediate Similarity	NPC295276
0.8182	Intermediate Similarity	NPC183546
0.8182	Intermediate Similarity	NPC294480
0.8171	Intermediate Similarity	NPC260301
0.8171	Intermediate Similarity	NPC307336
0.8171	Intermediate Similarity	NPC238227
0.8171	Intermediate Similarity	NPC138502
0.8161	Intermediate Similarity	NPC168231
0.8161	Intermediate Similarity	NPC28252
0.8161	Intermediate Similarity	NPC212843
0.8161	Intermediate Similarity	NPC55309
0.8152	Intermediate Similarity	NPC234564
0.8152	Intermediate Similarity	NPC155676
0.814	Intermediate Similarity	NPC474482
0.814	Intermediate Similarity	NPC474233
0.814	Intermediate Similarity	NPC74595
0.814	Intermediate Similarity	NPC475745
0.814	Intermediate Similarity	NPC264665
0.814	Intermediate Similarity	NPC475509
0.8132	Intermediate Similarity	NPC303863
0.8132	Intermediate Similarity	NPC47853
0.8125	Intermediate Similarity	NPC36310
0.8125	Intermediate Similarity	NPC47281
0.8118	Intermediate Similarity	NPC472504
0.8111	Intermediate Similarity	NPC198054
0.8111	Intermediate Similarity	NPC23434
0.8111	Intermediate Similarity	NPC250753
0.8111	Intermediate Similarity	NPC160506
0.8111	Intermediate Similarity	NPC471901
0.8105	Intermediate Similarity	NPC170615
0.8101	Intermediate Similarity	NPC477929
0.8095	Intermediate Similarity	NPC206735
0.8095	Intermediate Similarity	NPC164999
0.809	Intermediate Similarity	NPC475921
0.809	Intermediate Similarity	NPC474704
0.809	Intermediate Similarity	NPC281524
0.809	Intermediate Similarity	NPC271974
0.809	Intermediate Similarity	NPC247312
0.8085	Intermediate Similarity	NPC41971
0.8085	Intermediate Similarity	NPC108371
0.8085	Intermediate Similarity	NPC37047
0.8085	Intermediate Similarity	NPC180733
0.8072	Intermediate Similarity	NPC476810
0.8072	Intermediate Similarity	NPC476732
0.8072	Intermediate Similarity	NPC472502
0.8072	Intermediate Similarity	NPC239098
0.8072	Intermediate Similarity	NPC475
0.8072	Intermediate Similarity	NPC321690
0.8072	Intermediate Similarity	NPC199965
0.8072	Intermediate Similarity	NPC472500
0.8072	Intermediate Similarity	NPC472499
0.8072	Intermediate Similarity	NPC472501
0.8068	Intermediate Similarity	NPC159046
0.8068	Intermediate Similarity	NPC233836
0.8068	Intermediate Similarity	NPC96496
0.8068	Intermediate Similarity	NPC187376
0.8068	Intermediate Similarity	NPC312215
0.8068	Intermediate Similarity	NPC128644
0.8049	Intermediate Similarity	NPC20466
0.8046	Intermediate Similarity	NPC102292
0.8046	Intermediate Similarity	NPC76518
0.8046	Intermediate Similarity	NPC474083
0.8046	Intermediate Similarity	NPC98270
0.8043	Intermediate Similarity	NPC184848
0.8043	Intermediate Similarity	NPC69548
0.8043	Intermediate Similarity	NPC279974
0.8043	Intermediate Similarity	NPC98639
0.8041	Intermediate Similarity	NPC37600
0.8041	Intermediate Similarity	NPC50535
0.8025	Intermediate Similarity	NPC46610
0.8025	Intermediate Similarity	NPC167702
0.8025	Intermediate Similarity	NPC476736
0.8025	Intermediate Similarity	NPC18819
0.8025	Intermediate Similarity	NPC280026
0.8023	Intermediate Similarity	NPC175410
0.8023	Intermediate Similarity	NPC291320
0.8023	Intermediate Similarity	NPC471036
0.8023	Intermediate Similarity	NPC5280
0.8023	Intermediate Similarity	NPC118800
0.8022	Intermediate Similarity	NPC224060
0.8022	Intermediate Similarity	NPC206810
0.8022	Intermediate Similarity	NPC244356
0.8022	Intermediate Similarity	NPC291373
0.8022	Intermediate Similarity	NPC472496

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 NPC263974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1777
0.2-0.3	4182
0.3-0.4	2043
0.4-0.5	516
0.5-0.6	162
0.6-0.7	197
0.7-0.8	110
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD7520	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4788	Approved
0.8111	Intermediate Similarity	NPD8034	Phase 2
0.8111	Intermediate Similarity	NPD8035	Phase 2
0.8025	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6409	Approved
0.7955	Intermediate Similarity	NPD6684	Approved
0.7955	Intermediate Similarity	NPD5330	Approved
0.7955	Intermediate Similarity	NPD7146	Approved
0.7955	Intermediate Similarity	NPD7521	Approved
0.7955	Intermediate Similarity	NPD7334	Approved
0.7931	Intermediate Similarity	NPD3666	Approved
0.7931	Intermediate Similarity	NPD3133	Approved
0.7931	Intermediate Similarity	NPD4786	Approved
0.7931	Intermediate Similarity	NPD3665	Phase 1
0.7875	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD4245	Approved
0.7872	Intermediate Similarity	NPD6084	Phase 2
0.7872	Intermediate Similarity	NPD6083	Phase 2
0.7831	Intermediate Similarity	NPD6117	Approved
0.7826	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD5777	Approved
0.7778	Intermediate Similarity	NPD6903	Approved
0.775	Intermediate Similarity	NPD3698	Phase 2
0.7738	Intermediate Similarity	NPD6116	Phase 1
0.7711	Intermediate Similarity	NPD3702	Approved
0.7708	Intermediate Similarity	NPD7640	Approved
0.7708	Intermediate Similarity	NPD7639	Approved
0.7701	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD6114	Approved
0.7647	Intermediate Similarity	NPD6118	Approved
0.7647	Intermediate Similarity	NPD6115	Approved
0.7647	Intermediate Similarity	NPD6697	Approved
0.7604	Intermediate Similarity	NPD7638	Approved
0.7595	Intermediate Similarity	NPD4224	Phase 2
0.7561	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6098	Approved
0.7527	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.75	Intermediate Similarity	NPD5328	Approved
0.7474	Intermediate Similarity	NPD5695	Phase 3
0.7447	Intermediate Similarity	NPD4202	Approved
0.7444	Intermediate Similarity	NPD5329	Approved
0.7439	Intermediate Similarity	NPD4789	Approved
0.7423	Intermediate Similarity	NPD5696	Approved
0.7416	Intermediate Similarity	NPD5362	Discontinued
0.7391	Intermediate Similarity	NPD5737	Approved
0.7391	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.7353	Intermediate Similarity	NPD7320	Approved
0.7353	Intermediate Similarity	NPD6899	Approved
0.7353	Intermediate Similarity	NPD6881	Approved
0.7349	Intermediate Similarity	NPD6081	Approved
0.734	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD4197	Approved
0.7317	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6904	Approved
0.7312	Intermediate Similarity	NPD6080	Approved
0.7312	Intermediate Similarity	NPD6673	Approved
0.7282	Intermediate Similarity	NPD6372	Approved
0.7282	Intermediate Similarity	NPD6373	Approved
0.7255	Intermediate Similarity	NPD5701	Approved
0.7255	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7102	Approved
0.7212	Intermediate Similarity	NPD6883	Approved
0.7212	Intermediate Similarity	NPD7290	Approved
0.7209	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5208	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.72	Intermediate Similarity	NPD7632	Discontinued
0.7184	Intermediate Similarity	NPD6011	Approved
0.7174	Intermediate Similarity	NPD4688	Approved
0.7174	Intermediate Similarity	NPD4138	Approved
0.7174	Intermediate Similarity	NPD5279	Phase 3
0.7174	Intermediate Similarity	NPD4689	Approved
0.7174	Intermediate Similarity	NPD4690	Approved
0.7174	Intermediate Similarity	NPD5205	Approved
0.7174	Intermediate Similarity	NPD4693	Phase 3
0.717	Intermediate Similarity	NPD8133	Approved
0.7158	Intermediate Similarity	NPD5281	Approved
0.7158	Intermediate Similarity	NPD5693	Phase 1
0.7158	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7128	Intermediate Similarity	NPD6051	Approved
0.7115	Intermediate Similarity	NPD6013	Approved
0.7115	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD6012	Approved
0.7113	Intermediate Similarity	NPD5210	Approved
0.7113	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4629	Approved
0.7093	Intermediate Similarity	NPD7339	Approved
0.7093	Intermediate Similarity	NPD6942	Approved
0.7079	Intermediate Similarity	NPD7525	Registered
0.7075	Intermediate Similarity	NPD6882	Approved
0.7075	Intermediate Similarity	NPD8297	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6989	Remote Similarity	NPD5280	Approved
0.6989	Remote Similarity	NPD4694	Approved
0.6989	Remote Similarity	NPD5690	Phase 2
0.6988	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5360	Phase 3
0.6979	Remote Similarity	NPD6050	Approved
0.6979	Remote Similarity	NPD7637	Suspended
0.6957	Remote Similarity	NPD3668	Phase 3
0.6941	Remote Similarity	NPD4243	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD4270	Approved
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD4269	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3703	Phase 2
0.6875	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD5692	Phase 3
0.6875	Remote Similarity	NPD5207	Approved
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD4697	Phase 3
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5222	Approved
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6863	Remote Similarity	NPD4633	Approved
0.6854	Remote Similarity	NPD3617	Approved
0.6852	Remote Similarity	NPD4632	Approved
0.6848	Remote Similarity	NPD5331	Approved
0.6848	Remote Similarity	NPD5332	Approved
0.6837	Remote Similarity	NPD6001	Approved
0.6837	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7900	Approved
0.6835	Remote Similarity	NPD3198	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD4790	Discontinued
0.6813	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD4623	Approved
0.6809	Remote Similarity	NPD5786	Approved
0.6809	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD5694	Approved
0.6804	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD5173	Approved
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD4754	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6782	Remote Similarity	NPD4785	Approved
0.6782	Remote Similarity	NPD4784	Approved
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6778	Remote Similarity	NPD7645	Phase 2
0.6778	Remote Similarity	NPD4195	Approved
0.6778	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6335	Approved
0.6739	Remote Similarity	NPD6435	Approved
0.6727	Remote Similarity	NPD6274	Approved
0.6703	Remote Similarity	NPD6930	Phase 2
0.6703	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4252	Approved
0.6703	Remote Similarity	NPD4819	Approved
0.6703	Remote Similarity	NPD5368	Approved
0.6703	Remote Similarity	NPD4821	Approved
0.6703	Remote Similarity	NPD4820	Approved
0.6703	Remote Similarity	NPD6931	Approved
0.6703	Remote Similarity	NPD4822	Approved
0.6702	Remote Similarity	NPD5363	Approved
0.6698	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4768	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