NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	298.25
Volume:	340.982
LogP:	4.575
LogD:	2.431
LogS:	-3.828
# Rotatable Bonds:	15
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	2.699
Fsp3:	0.833
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:	-5.187
MDCK Permeability:	5.4742682550568134e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	97.05224609375%
Volume Distribution (VD):	0.508
Pgp-substrate:	0.9780857563018799%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.277
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	3.872
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.944
Carcinogencity:	0.11
Eye Corrosion:	0.802
Eye Irritation:	0.951
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC243532

Natural Product ID:	NPC243532
*Common Name:**	(Z,12R)-12-Hydroxyoctadec-9-Enoic Acid
IUPAC Name:	(Z,12R)-12-hydroxyoctadec-9-enoic acid
Synonyms:
Standard InCHIKey:	WBHHMMIMDMUBKC-QJWNTBNXSA-N
Standard InCHI:	InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1
SMILES:	CCCCCC[C@H](C/C=CCCCCCCCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3186422
PubChem CID:	643684
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26509914]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
EC50	2
Potency	36

Activity Type	# Activity
Individual Protein	7
Others	31

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4003	Individual Protein	G-protein coupled receptor 120	Homo sapiens	EC50	=	1318.26	nM	PMID[524097]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	19493.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	30106.5	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT869	Individual Protein	Free fatty acid receptor 1	Homo sapiens	EC50	=	11481.54	nM	PMID[524097]
NPT2	Others	Unspecified	""	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	30106.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	4896.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	12.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	""	Potency	n.a.	15484.5	nM	PubChem BioAssay data set

☑ 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 NPC243532 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	148
0.1-0.2	2039
0.2-0.3	11384
0.3-0.4	15225
0.4-0.5	7925
0.5-0.6	4520
0.6-0.7	1187
0.7-0.8	172
0.8-0.85	44
0.85-0.9	50
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC201939
0.9167	High Similarity	NPC328089
0.9167	High Similarity	NPC68343
0.9153	High Similarity	NPC321838
0.9032	High Similarity	NPC99619
0.9032	High Similarity	NPC26500
0.9016	High Similarity	NPC255863
0.9016	High Similarity	NPC136164
0.9016	High Similarity	NPC245947
0.8947	High Similarity	NPC477201
0.8929	High Similarity	NPC87564
0.8929	High Similarity	NPC261831
0.8929	High Similarity	NPC88966
0.8929	High Similarity	NPC290563
0.8929	High Similarity	NPC154245
0.8929	High Similarity	NPC32467
0.8929	High Similarity	NPC281972
0.8929	High Similarity	NPC424
0.8929	High Similarity	NPC85813
0.8929	High Similarity	NPC6095
0.8929	High Similarity	NPC25417
0.8852	High Similarity	NPC470320
0.8833	High Similarity	NPC320305
0.8833	High Similarity	NPC328776
0.8772	High Similarity	NPC52264
0.875	High Similarity	NPC294548
0.875	High Similarity	NPC70387
0.875	High Similarity	NPC321062
0.875	High Similarity	NPC36061
0.875	High Similarity	NPC1813
0.875	High Similarity	NPC139029
0.873	High Similarity	NPC330426
0.873	High Similarity	NPC148192
0.873	High Similarity	NPC127091
0.873	High Similarity	NPC22101
0.873	High Similarity	NPC271921
0.873	High Similarity	NPC104537
0.871	High Similarity	NPC318420
0.871	High Similarity	NPC326268
0.8621	High Similarity	NPC18951
0.8596	High Similarity	NPC137538
0.8594	High Similarity	NPC141481
0.8594	High Similarity	NPC48218
0.8594	High Similarity	NPC473559
0.8594	High Similarity	NPC324981
0.8571	High Similarity	NPC92114
0.8571	High Similarity	NPC281245
0.8548	High Similarity	NPC226592
0.85	High Similarity	NPC274927
0.85	High Similarity	NPC106851
0.8475	Intermediate Similarity	NPC323436
0.8462	Intermediate Similarity	NPC317583
0.8448	Intermediate Similarity	NPC10316
0.8448	Intermediate Similarity	NPC128061
0.8448	Intermediate Similarity	NPC200845
0.8448	Intermediate Similarity	NPC223677
0.8448	Intermediate Similarity	NPC28779
0.8438	Intermediate Similarity	NPC475443
0.8438	Intermediate Similarity	NPC473829
0.8421	Intermediate Similarity	NPC39633
0.8421	Intermediate Similarity	NPC309606
0.8421	Intermediate Similarity	NPC139545
0.8393	Intermediate Similarity	NPC262968
0.8361	Intermediate Similarity	NPC327112
0.8333	Intermediate Similarity	NPC42526
0.8333	Intermediate Similarity	NPC476660
0.8305	Intermediate Similarity	NPC187777
0.8305	Intermediate Similarity	NPC179764
0.8226	Intermediate Similarity	NPC477829
0.8214	Intermediate Similarity	NPC224227
0.8214	Intermediate Similarity	NPC59051
0.8182	Intermediate Similarity	NPC473772
0.8182	Intermediate Similarity	NPC143396
0.8167	Intermediate Similarity	NPC323597
0.8167	Intermediate Similarity	NPC211752
0.8167	Intermediate Similarity	NPC225929
0.8167	Intermediate Similarity	NPC323498
0.8136	Intermediate Similarity	NPC473863
0.8136	Intermediate Similarity	NPC274290
0.8136	Intermediate Similarity	NPC228473
0.8136	Intermediate Similarity	NPC54766
0.8103	Intermediate Similarity	NPC71761
0.8095	Intermediate Similarity	NPC54925
0.8088	Intermediate Similarity	NPC325627
0.8065	Intermediate Similarity	NPC143857
0.8065	Intermediate Similarity	NPC174447
0.8065	Intermediate Similarity	NPC235242
0.8065	Intermediate Similarity	NPC122521
0.8065	Intermediate Similarity	NPC251042
0.8065	Intermediate Similarity	NPC328311
0.8065	Intermediate Similarity	NPC229252
0.8036	Intermediate Similarity	NPC5413
0.8036	Intermediate Similarity	NPC149821
0.8	Intermediate Similarity	NPC327388
0.7971	Intermediate Similarity	NPC227396
0.7971	Intermediate Similarity	NPC474321
0.7937	Intermediate Similarity	NPC40082
0.7903	Intermediate Similarity	NPC329249
0.7879	Intermediate Similarity	NPC49863
0.7857	Intermediate Similarity	NPC91495
0.7857	Intermediate Similarity	NPC207292
0.7857	Intermediate Similarity	NPC180534
0.7846	Intermediate Similarity	NPC317881
0.7846	Intermediate Similarity	NPC476657
0.7846	Intermediate Similarity	NPC323045
0.7846	Intermediate Similarity	NPC476655
0.7846	Intermediate Similarity	NPC476654
0.7778	Intermediate Similarity	NPC321919
0.7778	Intermediate Similarity	NPC81896
0.7746	Intermediate Similarity	NPC279537
0.7727	Intermediate Similarity	NPC476659
0.7727	Intermediate Similarity	NPC328653
0.7727	Intermediate Similarity	NPC476656
0.7681	Intermediate Similarity	NPC320119
0.7679	Intermediate Similarity	NPC324004
0.7679	Intermediate Similarity	NPC328497
0.7667	Intermediate Similarity	NPC87394
0.7656	Intermediate Similarity	NPC174560
0.7656	Intermediate Similarity	NPC125312
0.7656	Intermediate Similarity	NPC113293
0.7656	Intermediate Similarity	NPC475984
0.7647	Intermediate Similarity	NPC470436
0.7627	Intermediate Similarity	NPC18357
0.7619	Intermediate Similarity	NPC322002
0.7576	Intermediate Similarity	NPC323477
0.7576	Intermediate Similarity	NPC320642
0.7571	Intermediate Similarity	NPC326024
0.7571	Intermediate Similarity	NPC470435
0.7544	Intermediate Similarity	NPC106872
0.7544	Intermediate Similarity	NPC216130
0.7538	Intermediate Similarity	NPC470965
0.7538	Intermediate Similarity	NPC29697
0.7536	Intermediate Similarity	NPC318766
0.7534	Intermediate Similarity	NPC218817
0.7534	Intermediate Similarity	NPC192006
0.7534	Intermediate Similarity	NPC11796
0.75	Intermediate Similarity	NPC273508
0.75	Intermediate Similarity	NPC209327
0.75	Intermediate Similarity	NPC117572
0.75	Intermediate Similarity	NPC76976
0.75	Intermediate Similarity	NPC469514
0.7467	Intermediate Similarity	NPC88735
0.7465	Intermediate Similarity	NPC92558
0.746	Intermediate Similarity	NPC267817
0.746	Intermediate Similarity	NPC34416
0.7458	Intermediate Similarity	NPC28205
0.7458	Intermediate Similarity	NPC470412
0.7458	Intermediate Similarity	NPC470410
0.7458	Intermediate Similarity	NPC284212
0.7458	Intermediate Similarity	NPC470411
0.7424	Intermediate Similarity	NPC476658
0.7419	Intermediate Similarity	NPC325977
0.7414	Intermediate Similarity	NPC207815
0.7414	Intermediate Similarity	NPC163345
0.7397	Intermediate Similarity	NPC281296
0.7391	Intermediate Similarity	NPC10758
0.7391	Intermediate Similarity	NPC236208
0.7391	Intermediate Similarity	NPC250928
0.7385	Intermediate Similarity	NPC325929
0.7385	Intermediate Similarity	NPC66460
0.7385	Intermediate Similarity	NPC271282
0.7368	Intermediate Similarity	NPC7414
0.7361	Intermediate Similarity	NPC260396
0.7353	Intermediate Similarity	NPC25298
0.7353	Intermediate Similarity	NPC478100
0.7353	Intermediate Similarity	NPC478097
0.7344	Intermediate Similarity	NPC322186
0.7333	Intermediate Similarity	NPC200446
0.7333	Intermediate Similarity	NPC161366
0.7333	Intermediate Similarity	NPC115418
0.7313	Intermediate Similarity	NPC176215
0.7313	Intermediate Similarity	NPC296436
0.7297	Intermediate Similarity	NPC121200
0.7297	Intermediate Similarity	NPC323249
0.7297	Intermediate Similarity	NPC260814
0.7297	Intermediate Similarity	NPC27949
0.7297	Intermediate Similarity	NPC39547
0.7288	Intermediate Similarity	NPC90904
0.7286	Intermediate Similarity	NPC477455
0.7286	Intermediate Similarity	NPC475310
0.7273	Intermediate Similarity	NPC477707
0.726	Intermediate Similarity	NPC190400
0.726	Intermediate Similarity	NPC49392
0.726	Intermediate Similarity	NPC477708
0.7246	Intermediate Similarity	NPC218477
0.7246	Intermediate Similarity	NPC476614
0.7237	Intermediate Similarity	NPC236649
0.7237	Intermediate Similarity	NPC191711
0.7237	Intermediate Similarity	NPC21693
0.7237	Intermediate Similarity	NPC47031
0.7222	Intermediate Similarity	NPC472966
0.7213	Intermediate Similarity	NPC477724
0.7213	Intermediate Similarity	NPC26102
0.7213	Intermediate Similarity	NPC187361
0.7213	Intermediate Similarity	NPC217188
0.7206	Intermediate Similarity	NPC83965
0.7206	Intermediate Similarity	NPC478101
0.72	Intermediate Similarity	NPC469747
0.72	Intermediate Similarity	NPC201225
0.72	Intermediate Similarity	NPC263574

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 NPC243532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	2762
0.2-0.3	3829
0.3-0.4	1678
0.4-0.5	558
0.5-0.6	135
0.6-0.7	47
0.7-0.8	13
0.8-0.85	3
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD3197	Phase 1
0.8929	High Similarity	NPD3196	Approved
0.8929	High Similarity	NPD3195	Phase 2
0.8929	High Similarity	NPD3194	Approved
0.8929	High Similarity	NPD4266	Approved
0.875	High Similarity	NPD3172	Approved
0.8393	Intermediate Similarity	NPD29	Approved
0.8393	Intermediate Similarity	NPD28	Approved
0.8361	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3173	Approved
0.7879	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD622	Approved
0.75	Intermediate Similarity	NPD3174	Discontinued
0.75	Intermediate Similarity	NPD4222	Approved
0.75	Intermediate Similarity	NPD39	Approved
0.7467	Intermediate Similarity	NPD5369	Approved
0.7368	Intermediate Similarity	NPD4270	Approved
0.7368	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD4252	Approved
0.7333	Intermediate Similarity	NPD5368	Approved
0.7297	Intermediate Similarity	NPD4268	Approved
0.7297	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4271	Approved
0.7273	Intermediate Similarity	NPD7154	Phase 3
0.7273	Intermediate Similarity	NPD5362	Discontinued
0.7241	Intermediate Similarity	NPD5343	Approved
0.7188	Intermediate Similarity	NPD6109	Phase 1
0.7143	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD5326	Phase 3
0.7105	Intermediate Similarity	NPD4820	Approved
0.7105	Intermediate Similarity	NPD4819	Approved
0.7105	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4822	Approved
0.7105	Intermediate Similarity	NPD4821	Approved
0.7089	Intermediate Similarity	NPD5363	Approved
0.7067	Intermediate Similarity	NPD3732	Approved
0.7	Intermediate Similarity	NPD5786	Approved
0.6835	Remote Similarity	NPD5332	Approved
0.6835	Remote Similarity	NPD5331	Approved
0.6825	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3728	Approved
0.6825	Remote Similarity	NPD3730	Approved
0.6795	Remote Similarity	NPD4790	Discontinued
0.6786	Remote Similarity	NPD2270	Approved
0.6765	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6101	Approved
0.6724	Remote Similarity	NPD6097	Approved
0.6724	Remote Similarity	NPD6096	Approved
0.6724	Remote Similarity	NPD2699	Approved
0.6714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3704	Approved
0.6714	Remote Similarity	NPD7331	Phase 2
0.6711	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD5785	Approved
0.6588	Remote Similarity	NPD6411	Approved
0.6588	Remote Similarity	NPD7983	Approved
0.6548	Remote Similarity	NPD5370	Suspended
0.6512	Remote Similarity	NPD5779	Approved
0.6512	Remote Similarity	NPD5778	Approved
0.6506	Remote Similarity	NPD4250	Approved
0.6506	Remote Similarity	NPD4251	Approved
0.6471	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD46	Approved
0.6447	Remote Similarity	NPD8039	Approved
0.6441	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9448	Phase 2
0.6429	Remote Similarity	NPD633	Phase 3
0.6395	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4249	Approved
0.6386	Remote Similarity	NPD6422	Discontinued
0.6341	Remote Similarity	NPD4786	Approved
0.6341	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3198	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.6292	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3206	Approved
0.6212	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7515	Phase 2
0.614	Remote Similarity	NPD9655	Approved
0.6136	Remote Similarity	NPD6399	Phase 3
0.6129	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7341	Phase 2
0.6094	Remote Similarity	NPD6927	Phase 3
0.6071	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD7909	Approved
0.5952	Remote Similarity	NPD3666	Approved
0.5952	Remote Similarity	NPD3133	Approved
0.5952	Remote Similarity	NPD3665	Phase 1
0.5909	Remote Similarity	NPD7838	Discovery
0.589	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6079	Approved
0.5843	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6684	Approved
0.5814	Remote Similarity	NPD7334	Approved
0.5814	Remote Similarity	NPD7146	Approved
0.5814	Remote Similarity	NPD5330	Approved
0.5814	Remote Similarity	NPD3618	Phase 1
0.5814	Remote Similarity	NPD7521	Approved
0.5814	Remote Similarity	NPD5279	Phase 3
0.5814	Remote Similarity	NPD6409	Approved
0.5806	Remote Similarity	NPD634	Phase 3
0.5795	Remote Similarity	NPD5328	Approved
0.5778	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3186	Phase 1
0.5714	Remote Similarity	NPD7144	Approved
0.5714	Remote Similarity	NPD7143	Approved
0.5699	Remote Similarity	NPD6084	Phase 2
0.5699	Remote Similarity	NPD7902	Approved
0.5699	Remote Similarity	NPD6083	Phase 2
0.5698	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD6924	Approved
0.5696	Remote Similarity	NPD6926	Approved
0.5682	Remote Similarity	NPD6903	Approved
0.5682	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD4695	Discontinued
0.5641	Remote Similarity	NPD7151	Approved
0.5641	Remote Similarity	NPD7152	Approved
0.5641	Remote Similarity	NPD7150	Approved
0.5638	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8264	Approved
0.5618	Remote Similarity	NPD5346	Phase 2
0.5618	Remote Similarity	NPD5347	Phase 2
0.5618	Remote Similarity	NPD7285	Clinical (unspecified phase)

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