NPASS Compound

Structure

NPC40082 OpenBabel07101718182D 22 21 0 0 0 0 0 0 0 0999 V2000 12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -0.5000 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 10.3923 0.0000 0.0000 C 0 0 0 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.2
Volume:	341.863
LogP:	3.476
LogD:	2.063
LogS:	-4.196
# Rotatable Bonds:	14
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	2.496
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.017
MDCK Permeability:	4.1390841943211854e-05
Pgp-inhibitor:	0.42
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.851
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	91.98360443115234%
Volume Distribution (VD):	0.494
Pgp-substrate:	2.2068443298339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.238
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	1.515
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.498
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.928
Carcinogencity:	0.454
Eye Corrosion:	0.753
Eye Irritation:	0.936
Respiratory Toxicity:	0.668

Download Data

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

Natural Product: NPC40082

Natural Product ID:	NPC40082
*Common Name:**	Ostopanic Acid
IUPAC Name:	(8E,10E)-7,12-dioxooctadeca-8,10-dienoic acid
Synonyms:
Standard InCHIKey:	WTLVYAWQAPUBFY-UTLPMFLDSA-N
Standard InCHI:	InChI=1S/C18H28O4/c1-2-3-4-6-11-16(19)13-9-10-14-17(20)12-7-5-8-15-18(21)22/h9-10,13-14H,2-8,11-12,15H2,1H3,(H,21,22)/b13-9+,14-10+
SMILES:	CCCCCCC(=O)/C=C/C=C/C(=O)CCCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478594
PubChem CID:	6440816
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655798]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6854337]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.5	ug ml-1	PMID[491470]

☑ 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 NPC40082 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	154
0.1-0.2	1814
0.2-0.3	10503
0.3-0.4	17411
0.4-0.5	8038
0.5-0.6	3749
0.6-0.7	839
0.7-0.8	132
0.8-0.85	20
0.85-0.9	28
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC251042
0.9825	High Similarity	NPC122521
0.9825	High Similarity	NPC174447
0.931	High Similarity	NPC106851
0.931	High Similarity	NPC274927
0.9153	High Similarity	NPC235242
0.9123	High Similarity	NPC325977
0.8906	High Similarity	NPC143396
0.8793	High Similarity	NPC18951
0.8793	High Similarity	NPC477201
0.8772	High Similarity	NPC322461
0.8667	High Similarity	NPC329550
0.8644	High Similarity	NPC225929
0.8596	High Similarity	NPC139029
0.8596	High Similarity	NPC36061
0.8596	High Similarity	NPC1813
0.8596	High Similarity	NPC294548
0.85	High Similarity	NPC34416
0.8448	Intermediate Similarity	NPC154245
0.8448	Intermediate Similarity	NPC88966
0.8448	Intermediate Similarity	NPC32467
0.8448	Intermediate Similarity	NPC281972
0.8448	Intermediate Similarity	NPC261831
0.8448	Intermediate Similarity	NPC87564
0.8448	Intermediate Similarity	NPC424
0.8448	Intermediate Similarity	NPC6095
0.8448	Intermediate Similarity	NPC25417
0.8448	Intermediate Similarity	NPC85813
0.8448	Intermediate Similarity	NPC290563
0.8421	Intermediate Similarity	NPC281245
0.8382	Intermediate Similarity	NPC474321
0.8281	Intermediate Similarity	NPC318420
0.8281	Intermediate Similarity	NPC326268
0.8276	Intermediate Similarity	NPC70387
0.8276	Intermediate Similarity	NPC321062
0.8226	Intermediate Similarity	NPC229252
0.8226	Intermediate Similarity	NPC143857
0.8182	Intermediate Similarity	NPC476614
0.8167	Intermediate Similarity	NPC187777
0.8167	Intermediate Similarity	NPC179764
0.8116	Intermediate Similarity	NPC227396
0.8103	Intermediate Similarity	NPC92114
0.8088	Intermediate Similarity	NPC288667
0.807	Intermediate Similarity	NPC224227
0.8	Intermediate Similarity	NPC136164
0.8	Intermediate Similarity	NPC245947
0.8	Intermediate Similarity	NPC228473
0.8	Intermediate Similarity	NPC473863
0.8	Intermediate Similarity	NPC255863
0.8	Intermediate Similarity	NPC274290
0.8	Intermediate Similarity	NPC54766
0.7937	Intermediate Similarity	NPC243532
0.7931	Intermediate Similarity	NPC262968
0.7895	Intermediate Similarity	NPC5413
0.7895	Intermediate Similarity	NPC149821
0.7879	Intermediate Similarity	NPC142423
0.7879	Intermediate Similarity	NPC308294
0.7812	Intermediate Similarity	NPC201939
0.7794	Intermediate Similarity	NPC236208
0.7759	Intermediate Similarity	NPC59051
0.7719	Intermediate Similarity	NPC207292
0.7719	Intermediate Similarity	NPC180534
0.7692	Intermediate Similarity	NPC53109
0.7692	Intermediate Similarity	NPC322457
0.7692	Intermediate Similarity	NPC477830
0.7692	Intermediate Similarity	NPC477707
0.7692	Intermediate Similarity	NPC143168
0.7681	Intermediate Similarity	NPC476660
0.7667	Intermediate Similarity	NPC39633
0.7667	Intermediate Similarity	NPC139545
0.7667	Intermediate Similarity	NPC309606
0.7656	Intermediate Similarity	NPC328311
0.7627	Intermediate Similarity	NPC477458
0.7576	Intermediate Similarity	NPC328089
0.7576	Intermediate Similarity	NPC470320
0.7576	Intermediate Similarity	NPC68343
0.7576	Intermediate Similarity	NPC7029
0.7538	Intermediate Similarity	NPC321838
0.7536	Intermediate Similarity	NPC262673
0.7536	Intermediate Similarity	NPC473772
0.7536	Intermediate Similarity	NPC67608
0.75	Intermediate Similarity	NPC18357
0.75	Intermediate Similarity	NPC148192
0.75	Intermediate Similarity	NPC330426
0.75	Intermediate Similarity	NPC99619
0.75	Intermediate Similarity	NPC260396
0.75	Intermediate Similarity	NPC22101
0.75	Intermediate Similarity	NPC127091
0.75	Intermediate Similarity	NPC104537
0.75	Intermediate Similarity	NPC26500
0.75	Intermediate Similarity	NPC271921
0.746	Intermediate Similarity	NPC281230
0.746	Intermediate Similarity	NPC192843
0.7432	Intermediate Similarity	NPC192006
0.7429	Intermediate Similarity	NPC42526
0.7429	Intermediate Similarity	NPC291062
0.7429	Intermediate Similarity	NPC94743
0.7429	Intermediate Similarity	NPC318766
0.7419	Intermediate Similarity	NPC52264
0.7419	Intermediate Similarity	NPC128061
0.7419	Intermediate Similarity	NPC223677
0.7419	Intermediate Similarity	NPC28779
0.7419	Intermediate Similarity	NPC10316
0.7419	Intermediate Similarity	NPC200845
0.7414	Intermediate Similarity	NPC91495
0.7391	Intermediate Similarity	NPC324981
0.7391	Intermediate Similarity	NPC48218
0.7391	Intermediate Similarity	NPC473559
0.7391	Intermediate Similarity	NPC141481
0.7385	Intermediate Similarity	NPC327112
0.7377	Intermediate Similarity	NPC71761
0.7368	Intermediate Similarity	NPC117572
0.7344	Intermediate Similarity	NPC267817
0.7333	Intermediate Similarity	NPC470412
0.7333	Intermediate Similarity	NPC28205
0.7333	Intermediate Similarity	NPC470410
0.7333	Intermediate Similarity	NPC284212
0.7313	Intermediate Similarity	NPC226592
0.7273	Intermediate Similarity	NPC174560
0.7273	Intermediate Similarity	NPC320305
0.7273	Intermediate Similarity	NPC125312
0.7273	Intermediate Similarity	NPC328776
0.7258	Intermediate Similarity	NPC137538
0.7258	Intermediate Similarity	NPC87394
0.7246	Intermediate Similarity	NPC60120
0.7246	Intermediate Similarity	NPC475443
0.7246	Intermediate Similarity	NPC243272
0.7246	Intermediate Similarity	NPC473829
0.7231	Intermediate Similarity	NPC329249
0.7222	Intermediate Similarity	NPC326024
0.7222	Intermediate Similarity	NPC325627
0.7206	Intermediate Similarity	NPC296436
0.7206	Intermediate Similarity	NPC176215
0.7206	Intermediate Similarity	NPC320642
0.7206	Intermediate Similarity	NPC476655
0.7206	Intermediate Similarity	NPC476657
0.7206	Intermediate Similarity	NPC476654
0.72	Intermediate Similarity	NPC74410
0.72	Intermediate Similarity	NPC182292
0.7183	Intermediate Similarity	NPC67183
0.7167	Intermediate Similarity	NPC474391
0.7164	Intermediate Similarity	NPC54925
0.7162	Intermediate Similarity	NPC180886
0.7143	Intermediate Similarity	NPC218477
0.7143	Intermediate Similarity	NPC125578
0.7143	Intermediate Similarity	NPC263382
0.7143	Intermediate Similarity	NPC146376
0.7143	Intermediate Similarity	NPC134385
0.7143	Intermediate Similarity	NPC53302
0.7123	Intermediate Similarity	NPC264178
0.7119	Intermediate Similarity	NPC216130
0.7105	Intermediate Similarity	NPC113363
0.7105	Intermediate Similarity	NPC164308
0.7101	Intermediate Similarity	NPC476656
0.7101	Intermediate Similarity	NPC476659
0.7101	Intermediate Similarity	NPC197089
0.7101	Intermediate Similarity	NPC83965
0.7083	Intermediate Similarity	NPC29328
0.7083	Intermediate Similarity	NPC67076
0.7083	Intermediate Similarity	NPC319163
0.7083	Intermediate Similarity	NPC320119
0.7077	Intermediate Similarity	NPC320421
0.7067	Intermediate Similarity	NPC316324
0.7067	Intermediate Similarity	NPC120776
0.7067	Intermediate Similarity	NPC240170
0.7059	Intermediate Similarity	NPC234767
0.7049	Intermediate Similarity	NPC48162
0.7042	Intermediate Similarity	NPC469914
0.7042	Intermediate Similarity	NPC94488
0.7042	Intermediate Similarity	NPC317583
0.7031	Intermediate Similarity	NPC472808
0.7031	Intermediate Similarity	NPC324224
0.7015	Intermediate Similarity	NPC477829
0.7	Intermediate Similarity	NPC474619
0.7	Intermediate Similarity	NPC278895
0.7	Intermediate Similarity	NPC49863
0.6986	Remote Similarity	NPC238948
0.6986	Remote Similarity	NPC329914
0.6986	Remote Similarity	NPC215745
0.6986	Remote Similarity	NPC12815
0.6986	Remote Similarity	NPC329890
0.6986	Remote Similarity	NPC474705
0.6984	Remote Similarity	NPC300121
0.6974	Remote Similarity	NPC169095
0.6962	Remote Similarity	NPC102197
0.6957	Remote Similarity	NPC323477
0.6957	Remote Similarity	NPC323045
0.6957	Remote Similarity	NPC317881
0.6935	Remote Similarity	NPC161366
0.6933	Remote Similarity	NPC266119
0.6933	Remote Similarity	NPC472967
0.6933	Remote Similarity	NPC279537
0.6933	Remote Similarity	NPC266159
0.6923	Remote Similarity	NPC278459
0.6923	Remote Similarity	NPC283502
0.6923	Remote Similarity	NPC90055
0.6923	Remote Similarity	NPC323436
0.6914	Remote Similarity	NPC234038
0.6892	Remote Similarity	NPC237591
0.6892	Remote Similarity	NPC92558

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 NPC40082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	2514
0.2-0.3	4067
0.3-0.4	1760
0.4-0.5	468
0.5-0.6	163
0.6-0.7	33
0.7-0.8	11
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD3172	Approved
0.8448	Intermediate Similarity	NPD3196	Approved
0.8448	Intermediate Similarity	NPD3194	Approved
0.8448	Intermediate Similarity	NPD4266	Approved
0.8448	Intermediate Similarity	NPD3195	Phase 2
0.7931	Intermediate Similarity	NPD29	Approved
0.7931	Intermediate Similarity	NPD28	Approved
0.7895	Intermediate Similarity	NPD3173	Approved
0.7778	Intermediate Similarity	NPD4756	Discovery
0.7719	Intermediate Similarity	NPD622	Approved
0.7692	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3197	Phase 1
0.7385	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3174	Discontinued
0.7368	Intermediate Similarity	NPD4222	Approved
0.7101	Intermediate Similarity	NPD7331	Phase 2
0.7069	Intermediate Similarity	NPD39	Approved
0.7	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5363	Approved
0.6724	Remote Similarity	NPD5326	Phase 3
0.662	Remote Similarity	NPD3704	Approved
0.6582	Remote Similarity	NPD5368	Approved
0.6538	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5281	Approved
0.6512	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD5369	Approved
0.6479	Remote Similarity	NPD7341	Phase 2
0.6452	Remote Similarity	NPD4220	Pre-registration
0.642	Remote Similarity	NPD4270	Approved
0.642	Remote Similarity	NPD4269	Approved
0.642	Remote Similarity	NPD6435	Approved
0.6395	Remote Similarity	NPD5785	Approved
0.6379	Remote Similarity	NPD2270	Approved
0.6375	Remote Similarity	NPD4252	Approved
0.6375	Remote Similarity	NPD4695	Discontinued
0.6364	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD633	Phase 3
0.6316	Remote Similarity	NPD9655	Approved
0.6316	Remote Similarity	NPD9448	Phase 2
0.629	Remote Similarity	NPD5343	Approved
0.6279	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5209	Approved
0.6173	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8039	Approved
0.6145	Remote Similarity	NPD7154	Phase 3
0.6145	Remote Similarity	NPD5362	Discontinued
0.6125	Remote Similarity	NPD3732	Approved
0.6125	Remote Similarity	NPD4271	Approved
0.6125	Remote Similarity	NPD4268	Approved
0.6119	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5786	Approved
0.6092	Remote Similarity	NPD6101	Approved
0.6092	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6109	Phase 1
0.6066	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4194	Approved
0.6056	Remote Similarity	NPD4193	Approved
0.6056	Remote Similarity	NPD4192	Approved
0.6056	Remote Similarity	NPD4191	Approved
0.6022	Remote Similarity	NPD2066	Phase 3
0.5977	Remote Similarity	NPD4518	Approved
0.5976	Remote Similarity	NPD4821	Approved
0.5976	Remote Similarity	NPD4822	Approved
0.5976	Remote Similarity	NPD4819	Approved
0.5976	Remote Similarity	NPD4820	Approved
0.5976	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7515	Phase 2
0.5955	Remote Similarity	NPD5694	Approved
0.5955	Remote Similarity	NPD7983	Approved
0.5955	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5280	Approved
0.593	Remote Similarity	NPD5690	Phase 2
0.593	Remote Similarity	NPD4694	Approved
0.593	Remote Similarity	NPD5279	Phase 3
0.5889	Remote Similarity	NPD5779	Approved
0.5889	Remote Similarity	NPD5778	Approved
0.5862	Remote Similarity	NPD3206	Approved
0.5862	Remote Similarity	NPD3573	Approved
0.5843	Remote Similarity	NPD6698	Approved
0.5843	Remote Similarity	NPD5207	Approved
0.5843	Remote Similarity	NPD5692	Phase 3
0.5843	Remote Similarity	NPD7838	Discovery
0.5843	Remote Similarity	NPD46	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4223	Phase 3
0.5824	Remote Similarity	NPD7748	Approved
0.5823	Remote Similarity	NPD4058	Approved
0.5806	Remote Similarity	NPD6097	Approved
0.5806	Remote Similarity	NPD6096	Approved
0.5778	Remote Similarity	NPD6050	Approved
0.5765	Remote Similarity	NPD5332	Approved
0.5765	Remote Similarity	NPD5331	Approved
0.5761	Remote Similarity	NPD5695	Phase 3
0.5747	Remote Similarity	NPD4519	Discontinued
0.5747	Remote Similarity	NPD4623	Approved
0.5747	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3728	Approved
0.5735	Remote Similarity	NPD3730	Approved
0.573	Remote Similarity	NPD5346	Phase 2
0.573	Remote Similarity	NPD5347	Phase 2
0.573	Remote Similarity	NPD5370	Suspended
0.5714	Remote Similarity	NPD226	Approved
0.5714	Remote Similarity	NPD4790	Discontinued
0.5714	Remote Similarity	NPD634	Phase 3
0.5699	Remote Similarity	NPD7614	Phase 1
0.5699	Remote Similarity	NPD7839	Suspended
0.5698	Remote Similarity	NPD3665	Phase 1
0.5698	Remote Similarity	NPD3666	Approved
0.5698	Remote Similarity	NPD4197	Approved
0.5698	Remote Similarity	NPD3133	Approved
0.5682	Remote Similarity	NPD4793	Discontinued
0.567	Remote Similarity	NPD1930	Approved
0.567	Remote Similarity	NPD6647	Phase 2
0.567	Remote Similarity	NPD1929	Approved
0.567	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4096	Approved
0.5658	Remote Similarity	NPD3709	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD9411	Phase 1
0.5638	Remote Similarity	NPD6083	Phase 2
0.5638	Remote Similarity	NPD7902	Approved
0.5638	Remote Similarity	NPD6084	Phase 2
0.5632	Remote Similarity	NPD1694	Approved
0.5632	Remote Similarity	NPD5329	Approved
0.5625	Remote Similarity	NPD4687	Approved
0.5618	Remote Similarity	NPD6672	Approved
0.5618	Remote Similarity	NPD5737	Approved
0.5604	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6079	Approved
0.56	Remote Similarity	NPD2685	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