NPASS Compound

Structure

NPC308828 OpenBabel07101718272D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.0000 2.0000 0.0000 C 0 0 0 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 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 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 1.7321 -3.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 1 6 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 18 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.822
LogD:	3.997
LogS:	-3.999
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	3.911
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.712
MDCK Permeability:	1.811283982533496e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.109
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	96.18402862548828%
Volume Distribution (VD):	3.491
Pgp-substrate:	4.615180015563965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.329
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.316
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.338
CYP2D6-substrate:	0.603
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.57

ADMET: Excretion

Clearance (CL):	4.021
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.682
Carcinogencity:	0.087
Eye Corrosion:	0.053
Eye Irritation:	0.921
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC308828

Natural Product ID:	NPC308828
*Common Name:**	(4Bs,8As,10R)-4B,8,8-Trimethyl-1-Propan-2-Yl-5,6,7,8A,9,10-Hexahydrophenanthrene-2,10-Diol
IUPAC Name:	(4bS,8aS,10R)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-2,10-diol
Synonyms:
Standard InCHIKey:	KTESLAVYKYMODC-GQIGUUNPSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12(2)17-14(21)8-7-13-18(17)15(22)11-16-19(3,4)9-6-10-20(13,16)5/h7-8,12,15-16,21-22H,6,9-11H2,1-5H3/t15-,16+,20-/m1/s1
SMILES:	O[C@@H]1C[C@H]2C(C)(C)CCC[C@@]2(c2c1c(C(C)C)c(O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462950
PubChem CID:	484434
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	Alaskan	n.a.	PMID[15387645]
NPO29845	Chamaecyparis nootkatensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
ED50	1
GI50	6
MIC	7

Activity Type	# Activity
Cell Line	7
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.7	ug ml-1	PMID[511217]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	1.8	ug.mL-1	PMID[511217]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	2.3	ug.mL-1	PMID[511217]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.8	ug.mL-1	PMID[511217]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	2.3	ug.mL-1	PMID[511217]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	2.6	ug.mL-1	PMID[511217]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	2.1	ug.mL-1	PMID[511217]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	16.0	ug.mL-1	PMID[511217]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	64.0	ug.mL-1	PMID[511217]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[511217]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	16.0	ug.mL-1	PMID[511217]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16.0	ug.mL-1	PMID[511217]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	8.0	ug.mL-1	PMID[511217]
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	8.0	ug.mL-1	PMID[511217]

☑ 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 NPC308828 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	279
0.1-0.2	1426
0.2-0.3	3080
0.3-0.4	8963
0.4-0.5	10428
0.5-0.6	9946
0.6-0.7	6819
0.7-0.8	1502
0.8-0.85	149
0.85-0.9	70
0.9-0.95	17
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC147179
0.9818	High Similarity	NPC469609
0.9817	High Similarity	NPC219112
0.9815	High Similarity	NPC268160
0.9636	High Similarity	NPC38893
0.9636	High Similarity	NPC308311
0.9636	High Similarity	NPC92
0.9636	High Similarity	NPC477137
0.9636	High Similarity	NPC469663
0.9554	High Similarity	NPC469644
0.955	High Similarity	NPC477136
0.9545	High Similarity	NPC192948
0.9545	High Similarity	NPC35797
0.9469	High Similarity	NPC260832
0.9469	High Similarity	NPC135467
0.9464	High Similarity	NPC471671
0.9444	High Similarity	NPC141782
0.9375	High Similarity	NPC304510
0.9375	High Similarity	NPC172219
0.9273	High Similarity	NPC228425
0.9224	High Similarity	NPC471794
0.9182	High Similarity	NPC260323
0.9182	High Similarity	NPC176279
0.9123	High Similarity	NPC164649
0.9123	High Similarity	NPC154030
0.9123	High Similarity	NPC48342
0.9107	High Similarity	NPC195922
0.9099	High Similarity	NPC250323
0.9091	High Similarity	NPC132720
0.9091	High Similarity	NPC13482
0.9052	High Similarity	NPC328504
0.9035	High Similarity	NPC16030
0.9009	High Similarity	NPC95716
0.9009	High Similarity	NPC77772
0.8992	High Similarity	NPC87985
0.8983	High Similarity	NPC198014
0.8983	High Similarity	NPC471187
0.8974	High Similarity	NPC253627
0.8947	High Similarity	NPC474387
0.8947	High Similarity	NPC474358
0.8947	High Similarity	NPC257540
0.8947	High Similarity	NPC137496
0.8947	High Similarity	NPC247858
0.8947	High Similarity	NPC154511
0.8947	High Similarity	NPC471668
0.8938	High Similarity	NPC471534
0.8929	High Similarity	NPC46940
0.8909	High Similarity	NPC11554
0.8908	High Similarity	NPC181334
0.8879	High Similarity	NPC151197
0.885	High Similarity	NPC715
0.8839	High Similarity	NPC470770
0.8839	High Similarity	NPC322753
0.8839	High Similarity	NPC266937
0.8818	High Similarity	NPC151477
0.8814	High Similarity	NPC142198
0.8814	High Similarity	NPC77569
0.8783	High Similarity	NPC141001
0.8761	High Similarity	NPC177962
0.8761	High Similarity	NPC62867
0.8739	High Similarity	NPC152946
0.8739	High Similarity	NPC262365
0.8739	High Similarity	NPC11250
0.8718	High Similarity	NPC323074
0.8718	High Similarity	NPC126002
0.8718	High Similarity	NPC93071
0.8696	High Similarity	NPC469719
0.8689	High Similarity	NPC471077
0.8678	High Similarity	NPC76119
0.8678	High Similarity	NPC4286
0.8661	High Similarity	NPC58865
0.8649	High Similarity	NPC472979
0.8649	High Similarity	NPC27252
0.8649	High Similarity	NPC320439
0.8644	High Similarity	NPC68339
0.8644	High Similarity	NPC477037
0.8644	High Similarity	NPC318581
0.8644	High Similarity	NPC325544
0.8636	High Similarity	NPC117115
0.8636	High Similarity	NPC243601
0.8607	High Similarity	NPC325294
0.8607	High Similarity	NPC71610
0.8607	High Similarity	NPC321822
0.8596	High Similarity	NPC302371
0.8584	High Similarity	NPC296683
0.8583	High Similarity	NPC478058
0.8583	High Similarity	NPC71094
0.8583	High Similarity	NPC321402
0.8571	High Similarity	NPC64642
0.8571	High Similarity	NPC472982
0.8571	High Similarity	NPC32322
0.8571	High Similarity	NPC149455
0.8571	High Similarity	NPC259703
0.8559	High Similarity	NPC271274
0.8559	High Similarity	NPC21594
0.8547	High Similarity	NPC299180
0.8545	High Similarity	NPC475225
0.8537	High Similarity	NPC476536
0.8534	High Similarity	NPC474486
0.8525	High Similarity	NPC124030
0.8525	High Similarity	NPC137750
0.8509	High Similarity	NPC308689
0.8509	High Similarity	NPC151537
0.85	High Similarity	NPC475166
0.85	High Similarity	NPC162935
0.85	High Similarity	NPC249340
0.8496	Intermediate Similarity	NPC314187
0.8482	Intermediate Similarity	NPC472980
0.8468	Intermediate Similarity	NPC138942
0.8455	Intermediate Similarity	NPC235762
0.8455	Intermediate Similarity	NPC471228
0.8455	Intermediate Similarity	NPC100414
0.8455	Intermediate Similarity	NPC43000
0.8448	Intermediate Similarity	NPC12656
0.844	Intermediate Similarity	NPC225506
0.844	Intermediate Similarity	NPC211885
0.843	Intermediate Similarity	NPC176208
0.843	Intermediate Similarity	NPC121168
0.8421	Intermediate Similarity	NPC44732
0.8417	Intermediate Similarity	NPC241001
0.8413	Intermediate Similarity	NPC312341
0.8413	Intermediate Similarity	NPC471851
0.8403	Intermediate Similarity	NPC42657
0.8387	Intermediate Similarity	NPC186889
0.8387	Intermediate Similarity	NPC262936
0.8387	Intermediate Similarity	NPC108164
0.8387	Intermediate Similarity	NPC30491
0.8378	Intermediate Similarity	NPC323810
0.8378	Intermediate Similarity	NPC288411
0.8362	Intermediate Similarity	NPC322239
0.8362	Intermediate Similarity	NPC317869
0.8349	Intermediate Similarity	NPC122005
0.8349	Intermediate Similarity	NPC252821
0.8349	Intermediate Similarity	NPC128723
0.8347	Intermediate Similarity	NPC154696
0.8346	Intermediate Similarity	NPC85595
0.8333	Intermediate Similarity	NPC196193
0.8333	Intermediate Similarity	NPC99734
0.8333	Intermediate Similarity	NPC318552
0.8333	Intermediate Similarity	NPC190501
0.8319	Intermediate Similarity	NPC66834
0.8319	Intermediate Similarity	NPC206
0.8304	Intermediate Similarity	NPC47284
0.8291	Intermediate Similarity	NPC107240
0.8291	Intermediate Similarity	NPC473137
0.8288	Intermediate Similarity	NPC19856
0.8288	Intermediate Similarity	NPC269212
0.8288	Intermediate Similarity	NPC168829
0.8281	Intermediate Similarity	NPC78307
0.8276	Intermediate Similarity	NPC473521
0.8276	Intermediate Similarity	NPC471179
0.8273	Intermediate Similarity	NPC174911
0.8273	Intermediate Similarity	NPC294741
0.8268	Intermediate Similarity	NPC476847
0.8264	Intermediate Similarity	NPC129176
0.8257	Intermediate Similarity	NPC77492
0.8257	Intermediate Similarity	NPC474073
0.823	Intermediate Similarity	NPC54765
0.823	Intermediate Similarity	NPC53740
0.823	Intermediate Similarity	NPC155072
0.822	Intermediate Similarity	NPC84999
0.822	Intermediate Similarity	NPC246760
0.8217	Intermediate Similarity	NPC202225
0.8214	Intermediate Similarity	NPC238696
0.8214	Intermediate Similarity	NPC272029
0.8203	Intermediate Similarity	NPC289624
0.8203	Intermediate Similarity	NPC59239
0.8203	Intermediate Similarity	NPC321086
0.8203	Intermediate Similarity	NPC27578
0.8198	Intermediate Similarity	NPC51015
0.8198	Intermediate Similarity	NPC252105
0.819	Intermediate Similarity	NPC469912
0.8189	Intermediate Similarity	NPC472793
0.8189	Intermediate Similarity	NPC99795
0.8182	Intermediate Similarity	NPC103916
0.8182	Intermediate Similarity	NPC299762
0.8182	Intermediate Similarity	NPC223451
0.8182	Intermediate Similarity	NPC478121
0.8182	Intermediate Similarity	NPC51333
0.8182	Intermediate Similarity	NPC92730
0.8182	Intermediate Similarity	NPC33675
0.8182	Intermediate Similarity	NPC132078
0.8182	Intermediate Similarity	NPC78119
0.8182	Intermediate Similarity	NPC216468
0.816	Intermediate Similarity	NPC470724
0.8154	Intermediate Similarity	NPC103082
0.8151	Intermediate Similarity	NPC261973
0.8151	Intermediate Similarity	NPC312105
0.8145	Intermediate Similarity	NPC265413
0.8145	Intermediate Similarity	NPC10154
0.8142	Intermediate Similarity	NPC219286
0.8142	Intermediate Similarity	NPC471350
0.8142	Intermediate Similarity	NPC99557
0.814	Intermediate Similarity	NPC227719
0.8136	Intermediate Similarity	NPC249270
0.813	Intermediate Similarity	NPC297057
0.8125	Intermediate Similarity	NPC153019
0.8125	Intermediate Similarity	NPC108497
0.8125	Intermediate Similarity	NPC78575
0.812	Intermediate Similarity	NPC228452

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 NPC308828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	895
0.2-0.3	1372
0.3-0.4	2825
0.4-0.5	2021
0.5-0.6	1231
0.6-0.7	433
0.7-0.8	91
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9123	High Similarity	NPD3091	Approved
0.8814	High Similarity	NPD3092	Approved
0.8678	High Similarity	NPD3094	Phase 2
0.8644	High Similarity	NPD3095	Discontinued
0.8435	Intermediate Similarity	NPD7635	Approved
0.8333	Intermediate Similarity	NPD4059	Approved
0.8333	Intermediate Similarity	NPD3019	Approved
0.8319	Intermediate Similarity	NPD2342	Discontinued
0.824	Intermediate Similarity	NPD5736	Approved
0.8182	Intermediate Similarity	NPD2932	Approved
0.8182	Intermediate Similarity	NPD3020	Approved
0.8108	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD1809	Phase 2
0.8	Intermediate Similarity	NPD288	Approved
0.7984	Intermediate Similarity	NPD6663	Approved
0.7982	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD3620	Phase 2
0.792	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD2860	Approved
0.7909	Intermediate Similarity	NPD844	Approved
0.789	Intermediate Similarity	NPD845	Approved
0.7863	Intermediate Similarity	NPD3021	Approved
0.7863	Intermediate Similarity	NPD3022	Approved
0.782	Intermediate Similarity	NPD7743	Approved
0.782	Intermediate Similarity	NPD7742	Approved
0.7818	Intermediate Similarity	NPD2933	Approved
0.7818	Intermediate Similarity	NPD2934	Approved
0.7805	Intermediate Similarity	NPD4093	Discontinued
0.7803	Intermediate Similarity	NPD4097	Suspended
0.7786	Intermediate Similarity	NPD4140	Approved
0.7778	Intermediate Similarity	NPD5327	Phase 3
0.776	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2286	Discontinued
0.7742	Intermediate Similarity	NPD1751	Approved
0.7734	Intermediate Similarity	NPD4624	Approved
0.7731	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5735	Approved
0.7712	Intermediate Similarity	NPD4750	Phase 3
0.768	Intermediate Similarity	NPD3026	Approved
0.768	Intermediate Similarity	NPD3023	Approved
0.7661	Intermediate Similarity	NPD3024	Approved
0.7661	Intermediate Similarity	NPD3025	Approved
0.7652	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2606	Approved
0.7615	Intermediate Similarity	NPD2605	Approved
0.7603	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4626	Approved
0.7591	Intermediate Similarity	NPD3638	Discontinued
0.7557	Intermediate Similarity	NPD5155	Approved
0.7557	Intermediate Similarity	NPD5156	Approved
0.7538	Intermediate Similarity	NPD3636	Approved
0.7538	Intermediate Similarity	NPD3635	Approved
0.7538	Intermediate Similarity	NPD2861	Phase 2
0.7538	Intermediate Similarity	NPD3637	Approved
0.7537	Intermediate Similarity	NPD6353	Approved
0.7519	Intermediate Similarity	NPD4060	Phase 1
0.7482	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3595	Approved
0.7481	Intermediate Similarity	NPD3594	Approved
0.7462	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2194	Approved
0.7462	Intermediate Similarity	NPD2195	Approved
0.746	Intermediate Similarity	NPD4589	Approved
0.7442	Intermediate Similarity	NPD6696	Suspended
0.7419	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1792	Phase 2
0.7414	Intermediate Similarity	NPD846	Approved
0.7414	Intermediate Similarity	NPD940	Approved
0.7398	Intermediate Similarity	NPD497	Approved
0.7381	Intermediate Similarity	NPD5691	Approved
0.7368	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1201	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2229	Approved
0.7317	Intermediate Similarity	NPD2234	Approved
0.7317	Intermediate Similarity	NPD2228	Approved
0.7317	Intermediate Similarity	NPD496	Approved
0.7317	Intermediate Similarity	NPD495	Approved
0.7317	Intermediate Similarity	NPD498	Approved
0.7302	Intermediate Similarity	NPD5303	Approved
0.7302	Intermediate Similarity	NPD5304	Approved
0.7293	Intermediate Similarity	NPD4625	Phase 3
0.728	Intermediate Similarity	NPD7340	Approved
0.7254	Intermediate Similarity	NPD7041	Phase 2
0.7254	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD3645	Discontinued
0.72	Intermediate Similarity	NPD6671	Approved
0.7194	Intermediate Similarity	NPD4721	Approved
0.7194	Intermediate Similarity	NPD4726	Approved
0.7194	Intermediate Similarity	NPD4725	Approved
0.7179	Intermediate Similarity	NPD1242	Phase 1
0.7177	Intermediate Similarity	NPD1398	Phase 1
0.7176	Intermediate Similarity	NPD1283	Approved
0.7167	Intermediate Similarity	NPD1444	Approved
0.7167	Intermediate Similarity	NPD1445	Approved
0.7165	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7741	Discontinued
0.7163	Intermediate Similarity	NPD7003	Approved
0.7163	Intermediate Similarity	NPD8166	Discontinued
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD2233	Approved
0.7154	Intermediate Similarity	NPD2232	Approved
0.7154	Intermediate Similarity	NPD2230	Approved
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7121	Intermediate Similarity	NPD1470	Approved
0.7109	Intermediate Similarity	NPD1651	Approved
0.7099	Intermediate Similarity	NPD4659	Approved
0.7092	Intermediate Similarity	NPD6674	Discontinued
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3657	Discovery
0.7077	Intermediate Similarity	NPD1610	Phase 2
0.7071	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6584	Phase 3
0.7063	Intermediate Similarity	NPD7157	Approved
0.705	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8651	Approved
0.704	Intermediate Similarity	NPD5283	Phase 1
0.7037	Intermediate Similarity	NPD3027	Phase 3
0.7034	Intermediate Similarity	NPD6273	Approved
0.7031	Intermediate Similarity	NPD7330	Discontinued
0.7021	Intermediate Similarity	NPD7037	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD8131	Suspended
0.6992	Remote Similarity	NPD4103	Phase 2
0.6992	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5699	Approved
0.6984	Remote Similarity	NPD9618	Approved
0.6984	Remote Similarity	NPD9614	Approved
0.6977	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD4749	Approved
0.695	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD5762	Approved
0.6947	Remote Similarity	NPD1281	Approved
0.6934	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD8032	Phase 2
0.6934	Remote Similarity	NPD6405	Approved
0.6929	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1753	Discontinued
0.6911	Remote Similarity	NPD2684	Approved
0.6906	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2157	Approved
0.6897	Remote Similarity	NPD2420	Approved
0.6897	Remote Similarity	NPD2421	Approved
0.6897	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD2235	Phase 2
0.6894	Remote Similarity	NPD2231	Phase 2
0.6891	Remote Similarity	NPD3028	Approved
0.6889	Remote Similarity	NPD4208	Discontinued
0.6884	Remote Similarity	NPD1613	Approved
0.6884	Remote Similarity	NPD3109	Approved
0.6884	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3110	Approved
0.6884	Remote Similarity	NPD2979	Phase 3
0.688	Remote Similarity	NPD228	Approved
0.687	Remote Similarity	NPD3143	Discontinued
0.6866	Remote Similarity	NPD1129	Approved
0.6866	Remote Similarity	NPD1131	Approved
0.6866	Remote Similarity	NPD1134	Approved
0.6866	Remote Similarity	NPD1133	Approved
0.6866	Remote Similarity	NPD1135	Approved
0.6861	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5451	Approved
0.6855	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5951	Approved
0.685	Remote Similarity	NPD1793	Approved
0.685	Remote Similarity	NPD1791	Approved
0.685	Remote Similarity	NPD2629	Approved
0.6846	Remote Similarity	NPD1357	Approved
0.6842	Remote Similarity	NPD6582	Phase 2
0.6842	Remote Similarity	NPD6583	Phase 3
0.6822	Remote Similarity	NPD9615	Approved
0.6822	Remote Similarity	NPD9616	Approved
0.6822	Remote Similarity	NPD9613	Approved
0.6818	Remote Similarity	NPD1611	Approved
0.6809	Remote Similarity	NPD4108	Discontinued
0.6797	Remote Similarity	NPD709	Approved
0.6794	Remote Similarity	NPD5125	Phase 3
0.6794	Remote Similarity	NPD2668	Approved
0.6794	Remote Similarity	NPD5126	Approved
0.6794	Remote Similarity	NPD9384	Approved
0.6794	Remote Similarity	NPD2667	Approved
0.6794	Remote Similarity	NPD7725	Approved
0.6794	Remote Similarity	NPD9381	Approved
0.6788	Remote Similarity	NPD7095	Approved
0.6783	Remote Similarity	NPD4256	Phase 2

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