NPASS Compound

Structure

NPC259156 OpenBabel07101718192D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 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 -1.7321 2.0000 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 -0.8660 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -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 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	5.703
LogD:	4.023
LogS:	-3.943
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	3.912
Fsp3:	0.75
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:	-4.734
MDCK Permeability:	2.0779407350346446e-05
Pgp-inhibitor:	0.706
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.68
30% Bioavailability (F30%):	0.43

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	96.05020141601562%
Volume Distribution (VD):	0.578
Pgp-substrate:	4.737344264984131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.573
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.189
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	1.853
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.787
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.936
Carcinogencity:	0.093
Eye Corrosion:	0.967
Eye Irritation:	0.89
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC259156

Natural Product ID:	NPC259156
*Common Name:**	(-)-(5S,9S,10S,13Z)-Labda-7,13-Dien-15-Oic Acid
IUPAC Name:	(Z)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:
Standard InCHIKey:	YUYHINCTHBQFIT-AZQUDNSPSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h8,13,16-17H,6-7,9-12H2,1-5H3,(H,21,22)/b14-13-/t16-,17-,20+/m0/s1
SMILES:	C/C(=C/C(=O)O)/CC[C@H]1C(=CC[C@H]2C(C)(C)CCC[C@]12C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233987
PubChem CID:	90670221
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
NPO33188	ageratina jocotepecana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24702233]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1000.0	ug.mL-1	PMID[484670]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10000.0	ug.mL-1	PMID[484670]

☑ 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 NPC259156 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	130
0.1-0.2	1629
0.2-0.3	11371
0.3-0.4	14736
0.4-0.5	8173
0.5-0.6	4918
0.6-0.7	1502
0.7-0.8	207
0.8-0.85	16
0.85-0.9	10
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242945
0.9516	High Similarity	NPC107258
0.8824	High Similarity	NPC130016
0.8824	High Similarity	NPC109576
0.8824	High Similarity	NPC56747
0.8824	High Similarity	NPC180015
0.8769	High Similarity	NPC255781
0.8571	High Similarity	NPC476346
0.8485	Intermediate Similarity	NPC185587
0.8451	Intermediate Similarity	NPC19907
0.8438	Intermediate Similarity	NPC326645
0.8438	Intermediate Similarity	NPC317177
0.8438	Intermediate Similarity	NPC317025
0.8438	Intermediate Similarity	NPC329416
0.8406	Intermediate Similarity	NPC133253
0.8333	Intermediate Similarity	NPC132542
0.8209	Intermediate Similarity	NPC81907
0.8143	Intermediate Similarity	NPC21944
0.8088	Intermediate Similarity	NPC254886
0.8056	Intermediate Similarity	NPC65650
0.8026	Intermediate Similarity	NPC472867
0.8026	Intermediate Similarity	NPC142253
0.8026	Intermediate Similarity	NPC256112
0.8026	Intermediate Similarity	NPC3511
0.8026	Intermediate Similarity	NPC472239
0.7922	Intermediate Similarity	NPC97913
0.791	Intermediate Similarity	NPC329698
0.7887	Intermediate Similarity	NPC160817
0.7879	Intermediate Similarity	NPC469728
0.7867	Intermediate Similarity	NPC242767
0.7838	Intermediate Similarity	NPC61952
0.7821	Intermediate Similarity	NPC87552
0.7821	Intermediate Similarity	NPC164577
0.7821	Intermediate Similarity	NPC472865
0.7812	Intermediate Similarity	NPC11130
0.7808	Intermediate Similarity	NPC476795
0.7792	Intermediate Similarity	NPC469804
0.7792	Intermediate Similarity	NPC2524
0.7792	Intermediate Similarity	NPC469805
0.7763	Intermediate Similarity	NPC281880
0.7733	Intermediate Similarity	NPC105197
0.7733	Intermediate Similarity	NPC179028
0.7733	Intermediate Similarity	NPC198240
0.7727	Intermediate Similarity	NPC176621
0.7722	Intermediate Similarity	NPC109528
0.7722	Intermediate Similarity	NPC8571
0.7703	Intermediate Similarity	NPC180886
0.7692	Intermediate Similarity	NPC476927
0.7692	Intermediate Similarity	NPC279639
0.7692	Intermediate Similarity	NPC3856
0.7692	Intermediate Similarity	NPC42476
0.7662	Intermediate Similarity	NPC159148
0.7662	Intermediate Similarity	NPC170303
0.7639	Intermediate Similarity	NPC181587
0.7632	Intermediate Similarity	NPC190211
0.76	Intermediate Similarity	NPC97377
0.7595	Intermediate Similarity	NPC306951
0.7595	Intermediate Similarity	NPC178025
0.7595	Intermediate Similarity	NPC472864
0.7595	Intermediate Similarity	NPC470800
0.7595	Intermediate Similarity	NPC181743
0.7595	Intermediate Similarity	NPC16287
0.7595	Intermediate Similarity	NPC19849
0.7568	Intermediate Similarity	NPC469803
0.7564	Intermediate Similarity	NPC469806
0.7564	Intermediate Similarity	NPC469799
0.7534	Intermediate Similarity	NPC35656
0.7532	Intermediate Similarity	NPC469798
0.7532	Intermediate Similarity	NPC469797
0.75	Intermediate Similarity	NPC60350
0.75	Intermediate Similarity	NPC239098
0.75	Intermediate Similarity	NPC42586
0.75	Intermediate Similarity	NPC329630
0.75	Intermediate Similarity	NPC473251
0.75	Intermediate Similarity	NPC34834
0.75	Intermediate Similarity	NPC275494
0.75	Intermediate Similarity	NPC471409
0.7468	Intermediate Similarity	NPC477124
0.7468	Intermediate Similarity	NPC49019
0.7467	Intermediate Similarity	NPC474463
0.7436	Intermediate Similarity	NPC278459
0.7436	Intermediate Similarity	NPC471898
0.7436	Intermediate Similarity	NPC477372
0.7436	Intermediate Similarity	NPC40228
0.7432	Intermediate Similarity	NPC168975
0.7432	Intermediate Similarity	NPC251970
0.7432	Intermediate Similarity	NPC20025
0.7432	Intermediate Similarity	NPC241854
0.7432	Intermediate Similarity	NPC75485
0.7432	Intermediate Similarity	NPC476046
0.7429	Intermediate Similarity	NPC279434
0.7424	Intermediate Similarity	NPC60772
0.7407	Intermediate Similarity	NPC475069
0.7407	Intermediate Similarity	NPC186975
0.7407	Intermediate Similarity	NPC175145
0.7407	Intermediate Similarity	NPC472869
0.7403	Intermediate Similarity	NPC170394
0.7377	Intermediate Similarity	NPC17518
0.7375	Intermediate Similarity	NPC248758
0.7368	Intermediate Similarity	NPC107039
0.7368	Intermediate Similarity	NPC471897
0.7368	Intermediate Similarity	NPC471899
0.7368	Intermediate Similarity	NPC165711
0.7349	Intermediate Similarity	NPC472240
0.7349	Intermediate Similarity	NPC262858
0.7349	Intermediate Similarity	NPC314727
0.7349	Intermediate Similarity	NPC146554
0.7342	Intermediate Similarity	NPC471218
0.7342	Intermediate Similarity	NPC320514
0.7342	Intermediate Similarity	NPC224455
0.7333	Intermediate Similarity	NPC192540
0.7333	Intermediate Similarity	NPC279666
0.7324	Intermediate Similarity	NPC176107
0.7324	Intermediate Similarity	NPC68703
0.7324	Intermediate Similarity	NPC69649
0.7317	Intermediate Similarity	NPC476293
0.7317	Intermediate Similarity	NPC476409
0.7317	Intermediate Similarity	NPC236618
0.7317	Intermediate Similarity	NPC136948
0.7297	Intermediate Similarity	NPC144947
0.7284	Intermediate Similarity	NPC35933
0.7273	Intermediate Similarity	NPC110094
0.7273	Intermediate Similarity	NPC74410
0.7273	Intermediate Similarity	NPC321514
0.7273	Intermediate Similarity	NPC260385
0.7273	Intermediate Similarity	NPC280654
0.725	Intermediate Similarity	NPC472440
0.725	Intermediate Similarity	NPC57370
0.725	Intermediate Similarity	NPC311070
0.725	Intermediate Similarity	NPC79945
0.725	Intermediate Similarity	NPC41539
0.7237	Intermediate Similarity	NPC112680
0.7237	Intermediate Similarity	NPC309399
0.7237	Intermediate Similarity	NPC69143
0.7237	Intermediate Similarity	NPC292589
0.7237	Intermediate Similarity	NPC89294
0.7237	Intermediate Similarity	NPC4509
0.7229	Intermediate Similarity	NPC474629
0.7229	Intermediate Similarity	NPC117122
0.7229	Intermediate Similarity	NPC472870
0.7229	Intermediate Similarity	NPC72397
0.7229	Intermediate Similarity	NPC48107
0.7222	Intermediate Similarity	NPC260474
0.7222	Intermediate Similarity	NPC188292
0.7215	Intermediate Similarity	NPC6663
0.7206	Intermediate Similarity	NPC127582
0.72	Intermediate Similarity	NPC103958
0.72	Intermediate Similarity	NPC183503
0.72	Intermediate Similarity	NPC213223
0.72	Intermediate Similarity	NPC301065
0.72	Intermediate Similarity	NPC161923
0.72	Intermediate Similarity	NPC283908
0.72	Intermediate Similarity	NPC104644
0.7195	Intermediate Similarity	NPC471219
0.7183	Intermediate Similarity	NPC176171
0.7183	Intermediate Similarity	NPC92327
0.7179	Intermediate Similarity	NPC199595
0.7179	Intermediate Similarity	NPC16394
0.7179	Intermediate Similarity	NPC327674
0.7179	Intermediate Similarity	NPC477371
0.7179	Intermediate Similarity	NPC231431
0.7176	Intermediate Similarity	NPC212948
0.7176	Intermediate Similarity	NPC477122
0.7162	Intermediate Similarity	NPC190035
0.716	Intermediate Similarity	NPC302360
0.716	Intermediate Similarity	NPC96095
0.716	Intermediate Similarity	NPC165064
0.7143	Intermediate Similarity	NPC472300
0.7143	Intermediate Similarity	NPC118011
0.7143	Intermediate Similarity	NPC91665
0.7143	Intermediate Similarity	NPC36668
0.7143	Intermediate Similarity	NPC262747
0.7143	Intermediate Similarity	NPC470734
0.7143	Intermediate Similarity	NPC475124
0.7143	Intermediate Similarity	NPC169275
0.7143	Intermediate Similarity	NPC266193
0.7143	Intermediate Similarity	NPC226066
0.7143	Intermediate Similarity	NPC257666
0.7143	Intermediate Similarity	NPC285371
0.7143	Intermediate Similarity	NPC52449
0.7143	Intermediate Similarity	NPC66344
0.7143	Intermediate Similarity	NPC262043
0.7143	Intermediate Similarity	NPC473756
0.7125	Intermediate Similarity	NPC268122
0.7125	Intermediate Similarity	NPC16321
0.7123	Intermediate Similarity	NPC139397
0.7123	Intermediate Similarity	NPC256846
0.7105	Intermediate Similarity	NPC476844
0.7105	Intermediate Similarity	NPC472327
0.7101	Intermediate Similarity	NPC60565
0.7097	Intermediate Similarity	NPC22765
0.7093	Intermediate Similarity	NPC38232
0.7093	Intermediate Similarity	NPC151722
0.7093	Intermediate Similarity	NPC214697
0.7089	Intermediate Similarity	NPC37038
0.7089	Intermediate Similarity	NPC271104
0.7089	Intermediate Similarity	NPC26139
0.7089	Intermediate Similarity	NPC104545
0.7083	Intermediate Similarity	NPC290350
0.7083	Intermediate Similarity	NPC4370

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 NPC259156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	1972
0.2-0.3	4591
0.3-0.4	1837
0.4-0.5	358
0.5-0.6	231
0.6-0.7	39
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD4191	Approved
0.8438	Intermediate Similarity	NPD4192	Approved
0.8438	Intermediate Similarity	NPD4194	Approved
0.8438	Intermediate Similarity	NPD4193	Approved
0.7143	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4137	Phase 3
0.7027	Intermediate Similarity	NPD4691	Approved
0.7027	Intermediate Similarity	NPD4747	Approved
0.6974	Remote Similarity	NPD5733	Approved
0.6866	Remote Similarity	NPD4219	Approved
0.6786	Remote Similarity	NPD4623	Approved
0.6786	Remote Similarity	NPD4519	Discontinued
0.6753	Remote Similarity	NPD4687	Approved
0.6753	Remote Similarity	NPD4058	Approved
0.675	Remote Similarity	NPD4195	Approved
0.6747	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6049	Phase 2
0.6742	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5276	Approved
0.6707	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD287	Approved
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6404	Discontinued
0.6591	Remote Similarity	NPD7515	Phase 2
0.6588	Remote Similarity	NPD7521	Approved
0.6588	Remote Similarity	NPD7334	Approved
0.6588	Remote Similarity	NPD7146	Approved
0.6588	Remote Similarity	NPD6409	Approved
0.6588	Remote Similarity	NPD6684	Approved
0.6588	Remote Similarity	NPD5330	Approved
0.6562	Remote Similarity	NPD4220	Pre-registration
0.6552	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4221	Approved
0.6506	Remote Similarity	NPD4223	Phase 3
0.6494	Remote Similarity	NPD4243	Approved
0.6471	Remote Similarity	NPD5329	Approved
0.6463	Remote Similarity	NPD4695	Discontinued
0.6452	Remote Similarity	NPD7640	Approved
0.6452	Remote Similarity	NPD7639	Approved
0.6444	Remote Similarity	NPD7748	Approved
0.6437	Remote Similarity	NPD6903	Approved
0.6437	Remote Similarity	NPD6672	Approved
0.6437	Remote Similarity	NPD5737	Approved
0.6437	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5284	Approved
0.6404	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6353	Remote Similarity	NPD3666	Approved
0.6353	Remote Similarity	NPD3133	Approved
0.6353	Remote Similarity	NPD4197	Approved
0.6353	Remote Similarity	NPD3665	Phase 1
0.6344	Remote Similarity	NPD7638	Approved
0.6329	Remote Similarity	NPD4784	Approved
0.6329	Remote Similarity	NPD4785	Approved
0.6322	Remote Similarity	NPD3573	Approved
0.625	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6237	Remote Similarity	NPD7902	Approved
0.6237	Remote Similarity	NPD6084	Phase 2
0.6237	Remote Similarity	NPD6083	Phase 2
0.6235	Remote Similarity	NPD3971	Phase 1
0.6222	Remote Similarity	NPD5693	Phase 1
0.6222	Remote Similarity	NPD6050	Approved
0.6222	Remote Similarity	NPD7637	Suspended
0.622	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3617	Approved
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6098	Approved
0.6207	Remote Similarity	NPD5690	Phase 2
0.6207	Remote Similarity	NPD3618	Phase 1
0.6207	Remote Similarity	NPD4694	Approved
0.6207	Remote Similarity	NPD4138	Approved
0.6207	Remote Similarity	NPD5205	Approved
0.6207	Remote Similarity	NPD4688	Approved
0.6207	Remote Similarity	NPD5280	Approved
0.6207	Remote Similarity	NPD4689	Approved
0.6207	Remote Similarity	NPD4690	Approved
0.6207	Remote Similarity	NPD4693	Phase 3
0.6196	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD8028	Phase 2
0.618	Remote Similarity	NPD5328	Approved
0.6173	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4225	Approved
0.6164	Remote Similarity	NPD368	Approved
0.6163	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6145	Remote Similarity	NPD7645	Phase 2
0.6133	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7614	Phase 1
0.6118	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD5692	Phase 3
0.6111	Remote Similarity	NPD5207	Approved
0.6098	Remote Similarity	NPD5776	Phase 2
0.6098	Remote Similarity	NPD6925	Approved
0.6092	Remote Similarity	NPD1694	Approved
0.6087	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7900	Approved
0.6071	Remote Similarity	NPD7514	Phase 3
0.6071	Remote Similarity	NPD7332	Phase 2
0.6061	Remote Similarity	NPD8262	Approved
0.6053	Remote Similarity	NPD7331	Phase 2
0.6049	Remote Similarity	NPD5275	Approved
0.6049	Remote Similarity	NPD4190	Phase 3
0.6047	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5694	Approved
0.6044	Remote Similarity	NPD6079	Approved
0.6026	Remote Similarity	NPD6922	Approved
0.6026	Remote Similarity	NPD6923	Approved
0.6024	Remote Similarity	NPD7145	Approved
0.6023	Remote Similarity	NPD5279	Phase 3
0.6023	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6902	Approved
0.5955	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6929	Approved
0.5949	Remote Similarity	NPD7143	Approved
0.5949	Remote Similarity	NPD6939	Phase 2
0.5949	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD7144	Approved
0.5926	Remote Similarity	NPD6924	Approved
0.5926	Remote Similarity	NPD6926	Approved
0.5914	Remote Similarity	NPD6001	Approved
0.5909	Remote Similarity	NPD1696	Phase 3
0.5882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6931	Approved
0.5882	Remote Similarity	NPD7525	Registered
0.5882	Remote Similarity	NPD6930	Phase 2
0.5875	Remote Similarity	NPD7152	Approved
0.5875	Remote Similarity	NPD7151	Approved
0.5875	Remote Similarity	NPD7150	Approved
0.5816	Remote Similarity	NPD7632	Discontinued
0.5814	Remote Similarity	NPD6898	Phase 1
0.5806	Remote Similarity	NPD4202	Approved
0.5806	Remote Similarity	NPD5779	Approved
0.5806	Remote Similarity	NPD5778	Approved
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5795	Remote Similarity	NPD3668	Phase 3
0.5789	Remote Similarity	NPD7732	Phase 3
0.5783	Remote Similarity	NPD6933	Approved
0.5761	Remote Similarity	NPD4096	Approved
0.5761	Remote Similarity	NPD5785	Approved
0.5745	Remote Similarity	NPD5707	Approved
0.573	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.573	Remote Similarity	NPD5363	Approved
0.5714	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD7341	Phase 2
0.5701	Remote Similarity	NPD7115	Discovery
0.5699	Remote Similarity	NPD6411	Approved
0.5698	Remote Similarity	NPD4821	Approved
0.5698	Remote Similarity	NPD4819	Approved
0.5698	Remote Similarity	NPD4820	Approved
0.5698	Remote Similarity	NPD4822	Approved
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD7320	Approved
0.5686	Remote Similarity	NPD6686	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5684	Remote Similarity	NPD5654	Approved
0.5684	Remote Similarity	NPD5210	Approved
0.5684	Remote Similarity	NPD4629	Approved
0.5682	Remote Similarity	NPD5362	Discontinued
0.5682	Remote Similarity	NPD5332	Approved
0.5682	Remote Similarity	NPD5331	Approved
0.5682	Remote Similarity	NPD6695	Phase 3
0.5657	Remote Similarity	NPD5211	Phase 2
0.5647	Remote Similarity	NPD4268	Approved
0.5647	Remote Similarity	NPD4271	Approved
0.5638	Remote Similarity	NPD5133	Approved
0.5632	Remote Similarity	NPD4692	Approved
0.5632	Remote Similarity	NPD4790	Discontinued
0.5632	Remote Similarity	NPD4139	Approved
0.5631	Remote Similarity	NPD6372	Approved
0.5631	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6373	Approved
0.5625	Remote Similarity	NPD5222	Approved
0.5625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4697	Phase 3
0.5625	Remote Similarity	NPD5221	Approved
0.5618	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6648	Approved
0.5606	Remote Similarity	NPD39	Approved
0.56	Remote Similarity	NPD6052	Approved

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