NPASS Compound

Structure

NPC475007 OpenBabel07101718272D 35 38 0 0 1 0 0 0 0 0999 V2000 2.3230 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3096 -5.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5175 -4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2574 -3.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5665 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9266 -2.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8973 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 2 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 10 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 1 6 0 0 0 22 29 1 6 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	3.58
LogD:	3.533
LogS:	-3.533
# Rotatable Bonds:	10
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	5.537
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.665
MDCK Permeability:	6.1493110479204915e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.81

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	90.1022720336914%
Volume Distribution (VD):	0.499
Pgp-substrate:	4.628988265991211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.702
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	2.372
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.762
Skin Sensitization:	0.915
Carcinogencity:	0.192
Eye Corrosion:	0.006
Eye Irritation:	0.159
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC475007

Natural Product ID:	NPC475007
*Common Name:**	Secaubrytriol
IUPAC Name:	n.a.
Synonyms:	secaubrytriol
Standard InCHIKey:	NFSDEMPRAKPPFK-HCQHQNCXSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-19(7-10-24(32)26(3,4)35)21-11-13-28(6)23-9-8-22(20(2)17-31)29(14-12-25(33)34)18-30(23,29)16-15-27(21,28)5/h19,21-24,31-32,35H,2,7-18H2,1,3-6H3,(H,33,34)/t19-,21-,22+,23-,24-,27-,28+,29-,30+/m1/s1
SMILES:	CC(CCC(C(C)(C)O)O)C1CCC2(C1(CCC34C2CCC(C3(C4)CCC(=O)O)C(=C)CO)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491709
PubChem CID:	44566395
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190447]
NPO4042	Gardenia aubryi	Species	Rubiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[515373]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	100000.0	nM	PMID[515373]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[515373]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[515373]

☑ 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 NPC475007 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	173
0.1-0.2	1434
0.2-0.3	6456
0.3-0.4	15484
0.4-0.5	5924
0.5-0.6	6428
0.6-0.7	5382
0.7-0.8	1332
0.8-0.85	59
0.85-0.9	18
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC70661
0.8966	High Similarity	NPC471747
0.8837	High Similarity	NPC255176
0.881	High Similarity	NPC194937
0.881	High Similarity	NPC476038
0.8795	High Similarity	NPC477858
0.8765	High Similarity	NPC321690
0.8706	High Similarity	NPC283733
0.8621	High Similarity	NPC254572
0.8621	High Similarity	NPC48824
0.8621	High Similarity	NPC250687
0.8621	High Similarity	NPC229407
0.8621	High Similarity	NPC16377
0.8588	High Similarity	NPC165064
0.8588	High Similarity	NPC263974
0.8571	High Similarity	NPC145143
0.8571	High Similarity	NPC170985
0.8523	High Similarity	NPC269267
0.8523	High Similarity	NPC220498
0.8519	High Similarity	NPC20466
0.8471	Intermediate Similarity	NPC245866
0.8462	Intermediate Similarity	NPC476174
0.8427	Intermediate Similarity	NPC469400
0.8415	Intermediate Similarity	NPC66105
0.8409	Intermediate Similarity	NPC117122
0.8409	Intermediate Similarity	NPC146937
0.8391	Intermediate Similarity	NPC2783
0.8391	Intermediate Similarity	NPC80590
0.8372	Intermediate Similarity	NPC130966
0.8333	Intermediate Similarity	NPC189520
0.8333	Intermediate Similarity	NPC476187
0.8315	Intermediate Similarity	NPC476733
0.8315	Intermediate Similarity	NPC128496
0.8315	Intermediate Similarity	NPC215029
0.8315	Intermediate Similarity	NPC155479
0.8295	Intermediate Similarity	NPC90652
0.8295	Intermediate Similarity	NPC264005
0.8295	Intermediate Similarity	NPC474174
0.8295	Intermediate Similarity	NPC251808
0.8295	Intermediate Similarity	NPC134197
0.8295	Intermediate Similarity	NPC33768
0.8295	Intermediate Similarity	NPC128644
0.8295	Intermediate Similarity	NPC269360
0.8293	Intermediate Similarity	NPC246445
0.8276	Intermediate Similarity	NPC294438
0.8276	Intermediate Similarity	NPC201655
0.8276	Intermediate Similarity	NPC264317
0.8276	Intermediate Similarity	NPC269638
0.8256	Intermediate Similarity	NPC471037
0.8242	Intermediate Similarity	NPC291373
0.8242	Intermediate Similarity	NPC243866
0.8235	Intermediate Similarity	NPC12933
0.8235	Intermediate Similarity	NPC232625
0.8235	Intermediate Similarity	NPC474484
0.8235	Intermediate Similarity	NPC103754
0.8214	Intermediate Similarity	NPC158846
0.8202	Intermediate Similarity	NPC474719
0.8202	Intermediate Similarity	NPC470417
0.8202	Intermediate Similarity	NPC183374
0.8202	Intermediate Similarity	NPC211162
0.8182	Intermediate Similarity	NPC12774
0.8182	Intermediate Similarity	NPC186975
0.8182	Intermediate Similarity	NPC155011
0.8182	Intermediate Similarity	NPC472505
0.8172	Intermediate Similarity	NPC29152
0.8152	Intermediate Similarity	NPC277399
0.8132	Intermediate Similarity	NPC470113
0.8125	Intermediate Similarity	NPC91369
0.8118	Intermediate Similarity	NPC170038
0.8118	Intermediate Similarity	NPC164999
0.8111	Intermediate Similarity	NPC116146
0.8111	Intermediate Similarity	NPC66344
0.8111	Intermediate Similarity	NPC213832
0.8111	Intermediate Similarity	NPC24772
0.8111	Intermediate Similarity	NPC474704
0.8111	Intermediate Similarity	NPC475921
0.8111	Intermediate Similarity	NPC32830
0.8111	Intermediate Similarity	NPC57954
0.8111	Intermediate Similarity	NPC214387
0.8105	Intermediate Similarity	NPC37047
0.8105	Intermediate Similarity	NPC41971
0.8105	Intermediate Similarity	NPC470074
0.8105	Intermediate Similarity	NPC180733
0.8095	Intermediate Similarity	NPC269543
0.8095	Intermediate Similarity	NPC247783
0.809	Intermediate Similarity	NPC236618
0.809	Intermediate Similarity	NPC142361
0.809	Intermediate Similarity	NPC474684
0.809	Intermediate Similarity	NPC136948
0.809	Intermediate Similarity	NPC96496
0.8085	Intermediate Similarity	NPC156546
0.8085	Intermediate Similarity	NPC107243
0.8068	Intermediate Similarity	NPC292553
0.8068	Intermediate Similarity	NPC471224
0.8068	Intermediate Similarity	NPC76518
0.8065	Intermediate Similarity	NPC263135
0.8065	Intermediate Similarity	NPC266431
0.8065	Intermediate Similarity	NPC288906
0.8049	Intermediate Similarity	NPC46610
0.8049	Intermediate Similarity	NPC18819
0.8046	Intermediate Similarity	NPC243347
0.8046	Intermediate Similarity	NPC472740
0.8022	Intermediate Similarity	NPC477149
0.8022	Intermediate Similarity	NPC477147
0.8022	Intermediate Similarity	NPC169933
0.8022	Intermediate Similarity	NPC289213
0.8021	Intermediate Similarity	NPC75941
0.8	Intermediate Similarity	NPC118987
0.8	Intermediate Similarity	NPC192744
0.8	Intermediate Similarity	NPC201459
0.8	Intermediate Similarity	NPC4309
0.8	Intermediate Similarity	NPC473155
0.8	Intermediate Similarity	NPC471900
0.8	Intermediate Similarity	NPC472870
0.8	Intermediate Similarity	NPC242864
0.7979	Intermediate Similarity	NPC234564
0.7979	Intermediate Similarity	NPC155676
0.7978	Intermediate Similarity	NPC322159
0.7978	Intermediate Similarity	NPC55309
0.7978	Intermediate Similarity	NPC473168
0.7978	Intermediate Similarity	NPC472869
0.7978	Intermediate Similarity	NPC324063
0.7978	Intermediate Similarity	NPC469994
0.7978	Intermediate Similarity	NPC472738
0.7978	Intermediate Similarity	NPC212843
0.7978	Intermediate Similarity	NPC187545
0.7978	Intermediate Similarity	NPC28252
0.7976	Intermediate Similarity	NPC238227
0.7976	Intermediate Similarity	NPC477919
0.7976	Intermediate Similarity	NPC474433
0.7976	Intermediate Similarity	NPC264602
0.7976	Intermediate Similarity	NPC180199
0.7976	Intermediate Similarity	NPC68828
0.7957	Intermediate Similarity	NPC469406
0.7957	Intermediate Similarity	NPC174051
0.7957	Intermediate Similarity	NPC67831
0.7955	Intermediate Similarity	NPC473157
0.7935	Intermediate Similarity	NPC45269
0.7935	Intermediate Similarity	NPC154101
0.7935	Intermediate Similarity	NPC262870
0.7931	Intermediate Similarity	NPC476292
0.7931	Intermediate Similarity	NPC474605
0.7931	Intermediate Similarity	NPC46881
0.7927	Intermediate Similarity	NPC244708
0.7927	Intermediate Similarity	NPC330659
0.7927	Intermediate Similarity	NPC161187
0.7917	Intermediate Similarity	NPC167974
0.7912	Intermediate Similarity	NPC271974
0.7912	Intermediate Similarity	NPC229871
0.7912	Intermediate Similarity	NPC469319
0.7912	Intermediate Similarity	NPC54689
0.7912	Intermediate Similarity	NPC262043
0.7912	Intermediate Similarity	NPC247312
0.7912	Intermediate Similarity	NPC2983
0.7895	Intermediate Similarity	NPC469432
0.7895	Intermediate Similarity	NPC57416
0.7895	Intermediate Similarity	NPC475894
0.7889	Intermediate Similarity	NPC187376
0.7889	Intermediate Similarity	NPC167877
0.7889	Intermediate Similarity	NPC4643
0.7889	Intermediate Similarity	NPC312215
0.7889	Intermediate Similarity	NPC233836
0.7889	Intermediate Similarity	NPC317590
0.7889	Intermediate Similarity	NPC159046
0.7882	Intermediate Similarity	NPC476732
0.7882	Intermediate Similarity	NPC472342
0.7882	Intermediate Similarity	NPC239098
0.7882	Intermediate Similarity	NPC199965
0.7875	Intermediate Similarity	NPC290445
0.7875	Intermediate Similarity	NPC36616
0.7872	Intermediate Similarity	NPC174948
0.7872	Intermediate Similarity	NPC53565
0.7872	Intermediate Similarity	NPC279974
0.7872	Intermediate Similarity	NPC173875
0.7872	Intermediate Similarity	NPC318282
0.7872	Intermediate Similarity	NPC293052
0.7872	Intermediate Similarity	NPC469995
0.7872	Intermediate Similarity	NPC84383
0.7865	Intermediate Similarity	NPC474083
0.7857	Intermediate Similarity	NPC476237
0.7857	Intermediate Similarity	NPC475050
0.7857	Intermediate Similarity	NPC476601
0.7849	Intermediate Similarity	NPC470376
0.7849	Intermediate Similarity	NPC244356
0.7849	Intermediate Similarity	NPC224060
0.7849	Intermediate Similarity	NPC471902
0.7849	Intermediate Similarity	NPC470375
0.7849	Intermediate Similarity	NPC474736
0.7849	Intermediate Similarity	NPC473690
0.7849	Intermediate Similarity	NPC476304
0.7849	Intermediate Similarity	NPC477855
0.7849	Intermediate Similarity	NPC287118
0.7841	Intermediate Similarity	NPC170862
0.7841	Intermediate Similarity	NPC86370
0.7841	Intermediate Similarity	NPC472743
0.7841	Intermediate Similarity	NPC472498
0.7841	Intermediate Similarity	NPC475726
0.7841	Intermediate Similarity	NPC477373
0.7841	Intermediate Similarity	NPC310470
0.7841	Intermediate Similarity	NPC215893

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 NPC475007 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	1915
0.2-0.3	4133
0.3-0.4	1985
0.4-0.5	517
0.5-0.6	161
0.6-0.7	234
0.7-0.8	48
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
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD4788	Approved
0.7753	Intermediate Similarity	NPD4786	Approved
0.7742	Intermediate Similarity	NPD8034	Phase 2
0.7742	Intermediate Similarity	NPD8035	Phase 2
0.766	Intermediate Similarity	NPD6399	Phase 3
0.7647	Intermediate Similarity	NPD6117	Approved
0.7619	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6116	Phase 1
0.7528	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD6083	Phase 2
0.7471	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6697	Approved
0.7471	Intermediate Similarity	NPD6115	Approved
0.7471	Intermediate Similarity	NPD6118	Approved
0.7471	Intermediate Similarity	NPD6114	Approved
0.7363	Intermediate Similarity	NPD3665	Phase 1
0.7363	Intermediate Similarity	NPD3666	Approved
0.7363	Intermediate Similarity	NPD3133	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6933	Approved
0.7234	Intermediate Similarity	NPD5737	Approved
0.7234	Intermediate Similarity	NPD6672	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.7204	Intermediate Similarity	NPD5330	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7188	Intermediate Similarity	NPD6079	Approved
0.7188	Intermediate Similarity	NPD7515	Phase 2
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7176	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6081	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3702	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7111	Intermediate Similarity	NPD7525	Registered
0.71	Intermediate Similarity	NPD5696	Approved
0.71	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD5329	Approved
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7059	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD4789	Approved
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7059	Intermediate Similarity	NPD4245	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7037	Intermediate Similarity	NPD8133	Approved
0.7021	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD5279	Phase 3
0.7011	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6924	Approved
0.701	Intermediate Similarity	NPD7637	Suspended
0.701	Intermediate Similarity	NPD5284	Approved
0.701	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD3668	Phase 3
0.6989	Remote Similarity	NPD4197	Approved
0.6988	Remote Similarity	NPD4224	Phase 2
0.6981	Remote Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD6673	Approved
0.6979	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6947	Remote Similarity	NPD7524	Approved
0.6944	Remote Similarity	NPD8297	Approved
0.6941	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3698	Phase 2
0.6932	Remote Similarity	NPD7339	Approved
0.6932	Remote Similarity	NPD6942	Approved
0.6923	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6931	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4697	Phase 3
0.6887	Remote Similarity	NPD6011	Approved
0.6882	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD4632	Approved
0.6869	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5286	Approved
0.6863	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD4696	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD5205	Approved
0.6842	Remote Similarity	NPD4138	Approved
0.6842	Remote Similarity	NPD4689	Approved
0.6842	Remote Similarity	NPD4688	Approved
0.6842	Remote Similarity	NPD4690	Approved
0.6842	Remote Similarity	NPD4693	Phase 3
0.6837	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD5173	Approved
0.6824	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5360	Phase 3
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6813	Remote Similarity	NPD6929	Approved
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6051	Approved
0.6796	Remote Similarity	NPD5223	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD6882	Approved
0.6782	Remote Similarity	NPD5777	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4225	Approved
0.6744	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6739	Remote Similarity	NPD4822	Approved
0.6731	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD5224	Approved
0.6731	Remote Similarity	NPD5225	Approved
0.6731	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD6686	Approved
0.6703	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD5332	Approved
0.6701	Remote Similarity	NPD5208	Approved
0.67	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7604	Phase 2
0.6606	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7750	Discontinued
0.6593	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD5776	Phase 2
0.6591	Remote Similarity	NPD4243	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD5692	Phase 3
0.6562	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD6893	Approved
0.6559	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD5368	Approved
0.6559	Remote Similarity	NPD7514	Phase 3
0.6556	Remote Similarity	NPD3703	Phase 2
0.6552	Remote Similarity	NPD6922	Approved
0.6552	Remote Similarity	NPD6923	Approved
0.6549	Remote Similarity	NPD6009	Approved
0.6542	Remote Similarity	NPD4767	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD6404	Discontinued
0.6526	Remote Similarity	NPD7154	Phase 3

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