NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	2.626
LogD:	1.917
LogS:	-4.149
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.654
Synthetic Accessibility Score:	4.285
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.655
MDCK Permeability:	2.245293217129074e-05
Pgp-inhibitor:	0.464
Pgp-substrate:	0.283
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	89.87220001220703%
Volume Distribution (VD):	1.233
Pgp-substrate:	10.909857749938965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.709
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.357
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.703
CYP2D6-inhibitor:	0.372
CYP2D6-substrate:	0.521
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.592

ADMET: Excretion

Clearance (CL):	6.054
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.183
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.45
Skin Sensitization:	0.916
Carcinogencity:	0.713
Eye Corrosion:	0.159
Eye Irritation:	0.636
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC197659

Natural Product ID:	NPC197659
*Common Name:**	(3R,4R,5R,7S)-Petasol
IUPAC Name:	(3S,4aR,5R,6R)-6-hydroxy-4a,5-dimethyl-3-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	AJFPOVBARCSOLH-MUYACECFSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)12-8-15(4)10(3)13(16)6-5-11(15)7-14(12)17/h7,10,12-13,16H,1,5-6,8H2,2-4H3/t10-,12-,13+,15+/m0/s1
SMILES:	CC(=C)[C@@H]1C[C@@]2(C)C(=CC1=O)CC[C@H]([C@@H]2C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581341
PubChem CID:	5275907
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO32481	Penicillium copticola	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25734623]
NPO40189	Ligularia rumicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30212198]

☑ 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	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	186010.0	nM	PMID[543857]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	44500.0	nM	PMID[543857]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	39320.0	nM	PMID[543857]

☑ 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 NPC197659 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	160
0.1-0.2	1076
0.2-0.3	5134
0.3-0.4	14142
0.4-0.5	9874
0.5-0.6	6494
0.6-0.7	4151
0.7-0.8	1485
0.8-0.85	137
0.85-0.9	33
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC172013
0.9221	High Similarity	NPC64600
0.92	High Similarity	NPC281138
0.92	High Similarity	NPC308038
0.9067	High Similarity	NPC178852
0.9054	High Similarity	NPC250621
0.9054	High Similarity	NPC263582
0.8919	High Similarity	NPC114236
0.8861	High Similarity	NPC470812
0.8846	High Similarity	NPC93590
0.8831	High Similarity	NPC148685
0.8831	High Similarity	NPC2482
0.8831	High Similarity	NPC157895
0.8831	High Similarity	NPC104120
0.8816	High Similarity	NPC62336
0.88	High Similarity	NPC470525
0.8784	High Similarity	NPC470299
0.875	High Similarity	NPC470574
0.8718	High Similarity	NPC121984
0.8718	High Similarity	NPC473420
0.8701	High Similarity	NPC229204
0.8684	High Similarity	NPC266193
0.8684	High Similarity	NPC257666
0.8684	High Similarity	NPC74995
0.8659	High Similarity	NPC471722
0.8659	High Similarity	NPC328539
0.8659	High Similarity	NPC472802
0.8642	High Similarity	NPC472985
0.8642	High Similarity	NPC472986
0.8642	High Similarity	NPC158393
0.8642	High Similarity	NPC72133
0.8642	High Similarity	NPC179591
0.8625	High Similarity	NPC85774
0.8625	High Similarity	NPC329043
0.8625	High Similarity	NPC214043
0.8625	High Similarity	NPC58841
0.8625	High Similarity	NPC321187
0.8625	High Similarity	NPC161423
0.8625	High Similarity	NPC227064
0.8625	High Similarity	NPC473246
0.8608	High Similarity	NPC48362
0.8571	High Similarity	NPC253561
0.8571	High Similarity	NPC80088
0.8554	High Similarity	NPC86319
0.8554	High Similarity	NPC119416
0.8554	High Similarity	NPC275740
0.8554	High Similarity	NPC472983
0.8553	High Similarity	NPC186554
0.8553	High Similarity	NPC76966
0.8537	High Similarity	NPC141292
0.8537	High Similarity	NPC475740
0.8519	High Similarity	NPC133954
0.8481	Intermediate Similarity	NPC226068
0.8481	Intermediate Similarity	NPC116797
0.8462	Intermediate Similarity	NPC152061
0.8452	Intermediate Similarity	NPC191684
0.8452	Intermediate Similarity	NPC473099
0.8452	Intermediate Similarity	NPC128672
0.8452	Intermediate Similarity	NPC134321
0.8452	Intermediate Similarity	NPC85173
0.8442	Intermediate Similarity	NPC203403
0.8442	Intermediate Similarity	NPC325946
0.8442	Intermediate Similarity	NPC34110
0.8434	Intermediate Similarity	NPC158778
0.8434	Intermediate Similarity	NPC206060
0.8434	Intermediate Similarity	NPC143767
0.8434	Intermediate Similarity	NPC310752
0.8434	Intermediate Similarity	NPC292491
0.8434	Intermediate Similarity	NPC131470
0.8434	Intermediate Similarity	NPC473229
0.8415	Intermediate Similarity	NPC31564
0.8415	Intermediate Similarity	NPC327115
0.8415	Intermediate Similarity	NPC474732
0.8415	Intermediate Similarity	NPC94666
0.8415	Intermediate Similarity	NPC474733
0.8415	Intermediate Similarity	NPC474778
0.8415	Intermediate Similarity	NPC145879
0.8415	Intermediate Similarity	NPC194417
0.8415	Intermediate Similarity	NPC472974
0.8415	Intermediate Similarity	NPC475862
0.8415	Intermediate Similarity	NPC74363
0.8415	Intermediate Similarity	NPC213412
0.8395	Intermediate Similarity	NPC237712
0.8375	Intermediate Similarity	NPC103486
0.8375	Intermediate Similarity	NPC151519
0.8354	Intermediate Similarity	NPC471514
0.8354	Intermediate Similarity	NPC472478
0.8354	Intermediate Similarity	NPC472301
0.8354	Intermediate Similarity	NPC476809
0.8353	Intermediate Similarity	NPC158030
0.8353	Intermediate Similarity	NPC65120
0.8353	Intermediate Similarity	NPC272746
0.8353	Intermediate Similarity	NPC145067
0.8353	Intermediate Similarity	NPC185936
0.8353	Intermediate Similarity	NPC233455
0.8353	Intermediate Similarity	NPC168027
0.8353	Intermediate Similarity	NPC116726
0.8353	Intermediate Similarity	NPC4036
0.8333	Intermediate Similarity	NPC207772
0.8333	Intermediate Similarity	NPC473999
0.8333	Intermediate Similarity	NPC475994
0.8333	Intermediate Similarity	NPC472973
0.8333	Intermediate Similarity	NPC31985
0.8333	Intermediate Similarity	NPC473100
0.8333	Intermediate Similarity	NPC471409
0.8333	Intermediate Similarity	NPC309603
0.8333	Intermediate Similarity	NPC275494
0.8333	Intermediate Similarity	NPC1015
0.8313	Intermediate Similarity	NPC136548
0.8313	Intermediate Similarity	NPC73064
0.8313	Intermediate Similarity	NPC58063
0.8312	Intermediate Similarity	NPC180886
0.8312	Intermediate Similarity	NPC472305
0.8293	Intermediate Similarity	NPC469948
0.8293	Intermediate Similarity	NPC476426
0.8293	Intermediate Similarity	NPC79573
0.8272	Intermediate Similarity	NPC169941
0.8272	Intermediate Similarity	NPC105173
0.8272	Intermediate Similarity	NPC251475
0.8272	Intermediate Similarity	NPC476082
0.8272	Intermediate Similarity	NPC278648
0.8256	Intermediate Similarity	NPC214756
0.8256	Intermediate Similarity	NPC272075
0.8256	Intermediate Similarity	NPC475255
0.8256	Intermediate Similarity	NPC295643
0.8256	Intermediate Similarity	NPC134826
0.8256	Intermediate Similarity	NPC69454
0.825	Intermediate Similarity	NPC119229
0.825	Intermediate Similarity	NPC136150
0.825	Intermediate Similarity	NPC3915
0.825	Intermediate Similarity	NPC473217
0.825	Intermediate Similarity	NPC475665
0.825	Intermediate Similarity	NPC14151
0.8235	Intermediate Similarity	NPC183283
0.8235	Intermediate Similarity	NPC48010
0.8235	Intermediate Similarity	NPC126993
0.8228	Intermediate Similarity	NPC474113
0.8228	Intermediate Similarity	NPC472490
0.8214	Intermediate Similarity	NPC474925
0.8214	Intermediate Similarity	NPC474677
0.8214	Intermediate Similarity	NPC471724
0.8205	Intermediate Similarity	NPC470428
0.8205	Intermediate Similarity	NPC165711
0.8205	Intermediate Similarity	NPC97377
0.8193	Intermediate Similarity	NPC95594
0.8193	Intermediate Similarity	NPC473226
0.8193	Intermediate Similarity	NPC198761
0.8193	Intermediate Similarity	NPC222613
0.8193	Intermediate Similarity	NPC118648
0.8193	Intermediate Similarity	NPC235341
0.8193	Intermediate Similarity	NPC470955
0.8193	Intermediate Similarity	NPC73038
0.8193	Intermediate Similarity	NPC325594
0.8193	Intermediate Similarity	NPC475022
0.8193	Intermediate Similarity	NPC6979
0.8193	Intermediate Similarity	NPC94755
0.8193	Intermediate Similarity	NPC477579
0.8193	Intermediate Similarity	NPC82979
0.8171	Intermediate Similarity	NPC59453
0.8171	Intermediate Similarity	NPC180834
0.8171	Intermediate Similarity	NPC82902
0.8171	Intermediate Similarity	NPC221758
0.8171	Intermediate Similarity	NPC476412
0.8171	Intermediate Similarity	NPC40687
0.8161	Intermediate Similarity	NPC23170
0.8161	Intermediate Similarity	NPC111015
0.8161	Intermediate Similarity	NPC245972
0.8161	Intermediate Similarity	NPC196227
0.8161	Intermediate Similarity	NPC471207
0.8161	Intermediate Similarity	NPC196485
0.8158	Intermediate Similarity	NPC247586
0.8158	Intermediate Similarity	NPC186042
0.8148	Intermediate Similarity	NPC310989
0.8148	Intermediate Similarity	NPC73882
0.8148	Intermediate Similarity	NPC470813
0.8148	Intermediate Similarity	NPC212083
0.814	Intermediate Similarity	NPC472975
0.814	Intermediate Similarity	NPC63748
0.814	Intermediate Similarity	NPC233116
0.814	Intermediate Similarity	NPC131872
0.814	Intermediate Similarity	NPC99380
0.814	Intermediate Similarity	NPC473998
0.814	Intermediate Similarity	NPC475806
0.814	Intermediate Similarity	NPC472978
0.8133	Intermediate Similarity	NPC92801
0.8133	Intermediate Similarity	NPC173321
0.8125	Intermediate Similarity	NPC45495
0.8125	Intermediate Similarity	NPC108955
0.8125	Intermediate Similarity	NPC469637
0.8125	Intermediate Similarity	NPC271104
0.8118	Intermediate Similarity	NPC477943
0.8118	Intermediate Similarity	NPC186688
0.8118	Intermediate Similarity	NPC26959
0.8118	Intermediate Similarity	NPC69627
0.8118	Intermediate Similarity	NPC472971
0.8118	Intermediate Similarity	NPC472970
0.8118	Intermediate Similarity	NPC268406
0.8101	Intermediate Similarity	NPC476949
0.8101	Intermediate Similarity	NPC297996
0.8101	Intermediate Similarity	NPC74410

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 NPC197659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1542
0.2-0.3	3922
0.3-0.4	2428
0.4-0.5	653
0.5-0.6	199
0.6-0.7	188
0.7-0.8	61
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD3618	Phase 1
0.8625	High Similarity	NPD3665	Phase 1
0.8625	High Similarity	NPD3133	Approved
0.8625	High Similarity	NPD3666	Approved
0.8554	High Similarity	NPD5328	Approved
0.8375	Intermediate Similarity	NPD3667	Approved
0.8353	Intermediate Similarity	NPD7515	Phase 2
0.8353	Intermediate Similarity	NPD6079	Approved
0.8256	Intermediate Similarity	NPD4202	Approved
0.8193	Intermediate Similarity	NPD5279	Phase 3
0.8171	Intermediate Similarity	NPD4786	Approved
0.7978	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD5221	Approved
0.7978	Intermediate Similarity	NPD5222	Approved
0.7978	Intermediate Similarity	NPD4697	Phase 3
0.7955	Intermediate Similarity	NPD7748	Approved
0.7927	Intermediate Similarity	NPD4223	Phase 3
0.7927	Intermediate Similarity	NPD4221	Approved
0.7907	Intermediate Similarity	NPD4753	Phase 2
0.7901	Intermediate Similarity	NPD4695	Discontinued
0.7889	Intermediate Similarity	NPD4755	Approved
0.7889	Intermediate Similarity	NPD5173	Approved
0.7765	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4197	Approved
0.7717	Intermediate Similarity	NPD5286	Approved
0.7717	Intermediate Similarity	NPD4700	Approved
0.7717	Intermediate Similarity	NPD4696	Approved
0.7717	Intermediate Similarity	NPD5285	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7654	Intermediate Similarity	NPD3617	Approved
0.7647	Intermediate Similarity	NPD5329	Approved
0.7647	Intermediate Similarity	NPD1694	Approved
0.7634	Intermediate Similarity	NPD5223	Approved
0.7558	Intermediate Similarity	NPD5690	Phase 2
0.7558	Intermediate Similarity	NPD6409	Approved
0.7558	Intermediate Similarity	NPD4688	Approved
0.7558	Intermediate Similarity	NPD4690	Approved
0.7558	Intermediate Similarity	NPD4689	Approved
0.7558	Intermediate Similarity	NPD5280	Approved
0.7558	Intermediate Similarity	NPD6684	Approved
0.7558	Intermediate Similarity	NPD4138	Approved
0.7558	Intermediate Similarity	NPD4623	Approved
0.7558	Intermediate Similarity	NPD7146	Approved
0.7558	Intermediate Similarity	NPD4693	Phase 3
0.7558	Intermediate Similarity	NPD7521	Approved
0.7558	Intermediate Similarity	NPD7334	Approved
0.7558	Intermediate Similarity	NPD5205	Approved
0.7558	Intermediate Similarity	NPD4519	Discontinued
0.7558	Intermediate Similarity	NPD5330	Approved
0.7558	Intermediate Similarity	NPD4694	Approved
0.7553	Intermediate Similarity	NPD4633	Approved
0.7553	Intermediate Similarity	NPD5225	Approved
0.7553	Intermediate Similarity	NPD5226	Approved
0.7553	Intermediate Similarity	NPD5211	Phase 2
0.7553	Intermediate Similarity	NPD5224	Approved
0.7529	Intermediate Similarity	NPD3668	Phase 3
0.7474	Intermediate Similarity	NPD5174	Approved
0.7474	Intermediate Similarity	NPD4754	Approved
0.7474	Intermediate Similarity	NPD5175	Approved
0.7473	Intermediate Similarity	NPD4629	Approved
0.7473	Intermediate Similarity	NPD5210	Approved
0.747	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5141	Approved
0.7386	Intermediate Similarity	NPD6903	Approved
0.7386	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7331	Phase 2
0.7363	Intermediate Similarity	NPD7900	Approved
0.7363	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7645	Phase 2
0.732	Intermediate Similarity	NPD5739	Approved
0.732	Intermediate Similarity	NPD7128	Approved
0.732	Intermediate Similarity	NPD4767	Approved
0.732	Intermediate Similarity	NPD4768	Approved
0.732	Intermediate Similarity	NPD6675	Approved
0.732	Intermediate Similarity	NPD6402	Approved
0.7312	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6084	Phase 2
0.7308	Intermediate Similarity	NPD4137	Phase 3
0.7283	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD3573	Approved
0.7253	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD5701	Approved
0.7245	Intermediate Similarity	NPD5697	Approved
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7341	Phase 2
0.7215	Intermediate Similarity	NPD4691	Approved
0.7215	Intermediate Similarity	NPD4747	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7195	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6672	Approved
0.7191	Intermediate Similarity	NPD5737	Approved
0.7172	Intermediate Similarity	NPD5128	Approved
0.7172	Intermediate Similarity	NPD7320	Approved
0.7172	Intermediate Similarity	NPD6011	Approved
0.7172	Intermediate Similarity	NPD4730	Approved
0.7172	Intermediate Similarity	NPD5168	Approved
0.7172	Intermediate Similarity	NPD6881	Approved
0.7172	Intermediate Similarity	NPD6899	Approved
0.7172	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7111	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6013	Approved
0.71	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD6372	Approved
0.71	Intermediate Similarity	NPD6012	Approved
0.71	Intermediate Similarity	NPD6014	Approved
0.7073	Intermediate Similarity	NPD6942	Approved
0.7073	Intermediate Similarity	NPD7339	Approved
0.7059	Intermediate Similarity	NPD7525	Registered
0.7053	Intermediate Similarity	NPD7638	Approved
0.7053	Intermediate Similarity	NPD5696	Approved
0.7045	Intermediate Similarity	NPD1696	Phase 3
0.7033	Intermediate Similarity	NPD4096	Approved
0.703	Intermediate Similarity	NPD5248	Approved
0.703	Intermediate Similarity	NPD5250	Approved
0.703	Intermediate Similarity	NPD7102	Approved
0.703	Intermediate Similarity	NPD7290	Approved
0.703	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4634	Approved
0.703	Intermediate Similarity	NPD5251	Approved
0.703	Intermediate Similarity	NPD5247	Approved
0.703	Intermediate Similarity	NPD6883	Approved
0.703	Intermediate Similarity	NPD5169	Approved
0.703	Intermediate Similarity	NPD5135	Approved
0.703	Intermediate Similarity	NPD5249	Phase 3
0.7	Intermediate Similarity	NPD4518	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD7639	Approved
0.6977	Remote Similarity	NPD4692	Approved
0.6977	Remote Similarity	NPD4139	Approved
0.6961	Remote Similarity	NPD5127	Approved
0.6961	Remote Similarity	NPD5215	Approved
0.6961	Remote Similarity	NPD5217	Approved
0.6961	Remote Similarity	NPD6869	Approved
0.6961	Remote Similarity	NPD6649	Approved
0.6961	Remote Similarity	NPD6847	Approved
0.6961	Remote Similarity	NPD5216	Approved
0.6961	Remote Similarity	NPD8130	Phase 1
0.6961	Remote Similarity	NPD6617	Approved
0.6961	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6650	Approved
0.6951	Remote Similarity	NPD4058	Approved
0.6951	Remote Similarity	NPD4687	Approved
0.6951	Remote Similarity	NPD6926	Approved
0.6951	Remote Similarity	NPD5733	Approved
0.6951	Remote Similarity	NPD6924	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5276	Approved
0.69	Remote Similarity	NPD6412	Phase 2
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8297	Approved
0.6893	Remote Similarity	NPD6882	Approved
0.6892	Remote Similarity	NPD287	Approved
0.6882	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5290	Discontinued
0.6842	Remote Similarity	NPD368	Approved
0.6827	Remote Similarity	NPD4632	Approved
0.6824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5208	Approved
0.6809	Remote Similarity	NPD6001	Approved
0.6795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6933	Approved
0.6762	Remote Similarity	NPD5167	Approved
0.675	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6904	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6707	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6701	Remote Similarity	NPD4225	Approved
0.6698	Remote Similarity	NPD6274	Approved
0.6698	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD6922	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD6317	Approved
0.6636	Remote Similarity	NPD6009	Approved
0.6634	Remote Similarity	NPD6008	Approved
0.6632	Remote Similarity	NPD5282	Discontinued
0.6596	Remote Similarity	NPD5694	Approved
0.6596	Remote Similarity	NPD8034	Phase 2
0.6596	Remote Similarity	NPD6050	Approved
0.6596	Remote Similarity	NPD5693	Phase 1
0.6596	Remote Similarity	NPD8035	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