NPASS Compound

Structure

NPC65650 OpenBabel07101719252D 24 25 0 0 1 0 0 0 0 0999 V2000 1.6425 4.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7899 1.8827 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 4.2814 4.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 3.1730 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 0.1589 2.2071 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 2.0908 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3837 3.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 -1.7321 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 2 0 0 0 0 0 0 0 0 0 3.0567 2.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7638 2.2765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 3.9495 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 16 1 0 0 0 0 6 24 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 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 15 20 1 6 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 4 1 6 0 0 0 21 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.24
Volume:	370.484
LogP:	3.499
LogD:	3.141
LogS:	-4.342
# Rotatable Bonds:	5
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	4.214
Fsp3:	0.714
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:	-4.91
MDCK Permeability:	2.4409529942204244e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.766

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	92.8695297241211%
Volume Distribution (VD):	1.009
Pgp-substrate:	5.576509475708008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.384
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	3.808
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.531
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.391
Skin Sensitization:	0.964
Carcinogencity:	0.053
Eye Corrosion:	0.804
Eye Irritation:	0.71
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC65650

Natural Product ID:	NPC65650
*Common Name:**	2-Oxokolavenic Acid Methyl Ester
IUPAC Name:	methyl (E)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	SABQHVWRNLPVTQ-ZQTZVFAOSA-N
Standard InCHI:	InChI=1S/C21H32O3/c1-14(11-19(23)24-6)7-9-20(4)15(2)8-10-21(5)16(3)12-17(22)13-18(20)21/h11-12,15,18H,7-10,13H2,1-6H3/b14-11+/t15-,18-,20+,21+/m1/s1
SMILES:	C/C(=CC(=O)OC)/CC[C@@]1(C)[C@H](C)CC[C@@]2(C)C(=CC(=O)C[C@H]12)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581993
PubChem CID:	12096942
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO32573	dysoxylum gotadhora	Species	Meliaceae	Eukaryota	Leaves and Twigs	n.a.	n.a.	PMID[25945867]

☑ 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	1
Others	5

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	24.8	%	PMID[567447]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	35.3	%	PMID[567447]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	56.6	%	PMID[567447]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	45200.0	nM	PMID[567447]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	19.9	%	PMID[567447]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	19.4	%	PMID[567447]

☑ 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 NPC65650 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	188
0.1-0.2	1559
0.2-0.3	6934
0.3-0.4	15798
0.4-0.5	8421
0.5-0.6	6343
0.6-0.7	2888
0.7-0.8	520
0.8-0.85	31
0.85-0.9	9
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC20025
0.8889	High Similarity	NPC109576
0.8889	High Similarity	NPC56747
0.8889	High Similarity	NPC180015
0.8889	High Similarity	NPC130016
0.8831	High Similarity	NPC268122
0.8718	High Similarity	NPC474790
0.8718	High Similarity	NPC474976
0.8718	High Similarity	NPC118423
0.8649	High Similarity	NPC476346
0.863	High Similarity	NPC276336
0.8625	High Similarity	NPC220478
0.8571	High Similarity	NPC185587
0.8533	High Similarity	NPC40353
0.85	High Similarity	NPC189311
0.8493	Intermediate Similarity	NPC133253
0.8442	Intermediate Similarity	NPC190211
0.8421	Intermediate Similarity	NPC472300
0.8395	Intermediate Similarity	NPC168248
0.8354	Intermediate Similarity	NPC94200
0.8313	Intermediate Similarity	NPC284561
0.8312	Intermediate Similarity	NPC470052
0.8312	Intermediate Similarity	NPC105197
0.8293	Intermediate Similarity	NPC477228
0.8289	Intermediate Similarity	NPC19907
0.8289	Intermediate Similarity	NPC27205
0.825	Intermediate Similarity	NPC193198
0.8243	Intermediate Similarity	NPC21944
0.8228	Intermediate Similarity	NPC40228
0.8193	Intermediate Similarity	NPC196407
0.8125	Intermediate Similarity	NPC3511
0.8125	Intermediate Similarity	NPC472867
0.8125	Intermediate Similarity	NPC472239
0.8125	Intermediate Similarity	NPC142253
0.8116	Intermediate Similarity	NPC127582
0.8095	Intermediate Similarity	NPC5509
0.8095	Intermediate Similarity	NPC474844
0.8082	Intermediate Similarity	NPC188292
0.8082	Intermediate Similarity	NPC155198
0.8082	Intermediate Similarity	NPC260474
0.8077	Intermediate Similarity	NPC471220
0.8072	Intermediate Similarity	NPC75315
0.8072	Intermediate Similarity	NPC163016
0.8056	Intermediate Similarity	NPC259156
0.8056	Intermediate Similarity	NPC242945
0.8052	Intermediate Similarity	NPC473223
0.8052	Intermediate Similarity	NPC180886
0.8028	Intermediate Similarity	NPC285371
0.8028	Intermediate Similarity	NPC329698
0.8028	Intermediate Similarity	NPC475124
0.8025	Intermediate Similarity	NPC22611
0.8	Intermediate Similarity	NPC60565
0.8	Intermediate Similarity	NPC476369
0.8	Intermediate Similarity	NPC190035
0.8	Intermediate Similarity	NPC476437
0.8	Intermediate Similarity	NPC282293
0.8	Intermediate Similarity	NPC181587
0.7976	Intermediate Similarity	NPC226863
0.7976	Intermediate Similarity	NPC472302
0.7975	Intermediate Similarity	NPC471299
0.7973	Intermediate Similarity	NPC139397
0.7973	Intermediate Similarity	NPC256846
0.7971	Intermediate Similarity	NPC472304
0.7971	Intermediate Similarity	NPC276764
0.7952	Intermediate Similarity	NPC472863
0.7949	Intermediate Similarity	NPC470557
0.7949	Intermediate Similarity	NPC316500
0.7927	Intermediate Similarity	NPC87552
0.7927	Intermediate Similarity	NPC149869
0.7927	Intermediate Similarity	NPC474359
0.7927	Intermediate Similarity	NPC475100
0.7927	Intermediate Similarity	NPC30486
0.7917	Intermediate Similarity	NPC251118
0.7901	Intermediate Similarity	NPC321289
0.7901	Intermediate Similarity	NPC469805
0.7901	Intermediate Similarity	NPC200513
0.7901	Intermediate Similarity	NPC469804
0.7901	Intermediate Similarity	NPC186276
0.7901	Intermediate Similarity	NPC327969
0.7895	Intermediate Similarity	NPC474228
0.7895	Intermediate Similarity	NPC303613
0.7875	Intermediate Similarity	NPC195424
0.7875	Intermediate Similarity	NPC267517
0.7867	Intermediate Similarity	NPC282593
0.7867	Intermediate Similarity	NPC159577
0.7867	Intermediate Similarity	NPC2634
0.7867	Intermediate Similarity	NPC260040
0.7867	Intermediate Similarity	NPC307176
0.7867	Intermediate Similarity	NPC265782
0.7867	Intermediate Similarity	NPC251929
0.7867	Intermediate Similarity	NPC35734
0.7857	Intermediate Similarity	NPC181327
0.7848	Intermediate Similarity	NPC321514
0.7838	Intermediate Similarity	NPC87141
0.7838	Intermediate Similarity	NPC310992
0.7831	Intermediate Similarity	NPC8571
0.7826	Intermediate Similarity	NPC56905
0.7826	Intermediate Similarity	NPC27610
0.7821	Intermediate Similarity	NPC899
0.7821	Intermediate Similarity	NPC474463
0.7816	Intermediate Similarity	NPC242069
0.7816	Intermediate Similarity	NPC469939
0.7805	Intermediate Similarity	NPC279639
0.7805	Intermediate Similarity	NPC470047
0.7805	Intermediate Similarity	NPC470046
0.7805	Intermediate Similarity	NPC3856
0.7792	Intermediate Similarity	NPC306928
0.7792	Intermediate Similarity	NPC166797
0.7791	Intermediate Similarity	NPC159748
0.7791	Intermediate Similarity	NPC198818
0.7791	Intermediate Similarity	NPC101651
0.7791	Intermediate Similarity	NPC212679
0.7791	Intermediate Similarity	NPC220454
0.7791	Intermediate Similarity	NPC8062
0.7791	Intermediate Similarity	NPC469595
0.7778	Intermediate Similarity	NPC469662
0.7778	Intermediate Similarity	NPC14203
0.7778	Intermediate Similarity	NPC278459
0.7778	Intermediate Similarity	NPC471898
0.7778	Intermediate Similarity	NPC477372
0.7778	Intermediate Similarity	NPC475833
0.7778	Intermediate Similarity	NPC229584
0.7765	Intermediate Similarity	NPC215831
0.7765	Intermediate Similarity	NPC24816
0.7763	Intermediate Similarity	NPC115023
0.7763	Intermediate Similarity	NPC54123
0.7763	Intermediate Similarity	NPC474562
0.7763	Intermediate Similarity	NPC257618
0.7763	Intermediate Similarity	NPC160817
0.775	Intermediate Similarity	NPC150646
0.7738	Intermediate Similarity	NPC195640
0.7733	Intermediate Similarity	NPC286814
0.7727	Intermediate Similarity	NPC38830
0.7727	Intermediate Similarity	NPC470697
0.7727	Intermediate Similarity	NPC476415
0.7722	Intermediate Similarity	NPC165711
0.7722	Intermediate Similarity	NPC97377
0.7711	Intermediate Similarity	NPC320801
0.7711	Intermediate Similarity	NPC178025
0.7711	Intermediate Similarity	NPC16287
0.7711	Intermediate Similarity	NPC181743
0.7703	Intermediate Similarity	NPC290350
0.7703	Intermediate Similarity	NPC4370
0.7701	Intermediate Similarity	NPC473944
0.7692	Intermediate Similarity	NPC244166
0.7692	Intermediate Similarity	NPC473171
0.7692	Intermediate Similarity	NPC469803
0.7683	Intermediate Similarity	NPC469799
0.7683	Intermediate Similarity	NPC320514
0.7683	Intermediate Similarity	NPC471218
0.7683	Intermediate Similarity	NPC240302
0.7683	Intermediate Similarity	NPC469806
0.7683	Intermediate Similarity	NPC100297
0.7674	Intermediate Similarity	NPC73995
0.7674	Intermediate Similarity	NPC118011
0.7674	Intermediate Similarity	NPC36668
0.7674	Intermediate Similarity	NPC174342
0.7674	Intermediate Similarity	NPC173042
0.7671	Intermediate Similarity	NPC107258
0.7662	Intermediate Similarity	NPC251705
0.7662	Intermediate Similarity	NPC470045
0.7662	Intermediate Similarity	NPC470044
0.7654	Intermediate Similarity	NPC469797
0.7654	Intermediate Similarity	NPC469798
0.7647	Intermediate Similarity	NPC171722
0.7647	Intermediate Similarity	NPC312561
0.764	Intermediate Similarity	NPC295347
0.7639	Intermediate Similarity	NPC197238
0.7639	Intermediate Similarity	NPC288253
0.7639	Intermediate Similarity	NPC202118
0.7625	Intermediate Similarity	NPC469996
0.7625	Intermediate Similarity	NPC4827
0.7625	Intermediate Similarity	NPC74410
0.7625	Intermediate Similarity	NPC115515
0.7625	Intermediate Similarity	NPC179028
0.7625	Intermediate Similarity	NPC275494
0.7625	Intermediate Similarity	NPC471409
0.7619	Intermediate Similarity	NPC177932
0.7619	Intermediate Similarity	NPC60350
0.7619	Intermediate Similarity	NPC106416
0.7619	Intermediate Similarity	NPC470048
0.7619	Intermediate Similarity	NPC86316
0.7619	Intermediate Similarity	NPC65661
0.7619	Intermediate Similarity	NPC323765
0.7614	Intermediate Similarity	NPC472871
0.7614	Intermediate Similarity	NPC115021
0.7614	Intermediate Similarity	NPC169343
0.7614	Intermediate Similarity	NPC475657
0.76	Intermediate Similarity	NPC39157
0.76	Intermediate Similarity	NPC20610
0.76	Intermediate Similarity	NPC296697
0.76	Intermediate Similarity	NPC142754
0.76	Intermediate Similarity	NPC82477
0.7595	Intermediate Similarity	NPC4509
0.7595	Intermediate Similarity	NPC69408
0.759	Intermediate Similarity	NPC97913
0.759	Intermediate Similarity	NPC49019
0.759	Intermediate Similarity	NPC41539
0.7586	Intermediate Similarity	NPC471818
0.7586	Intermediate Similarity	NPC51486

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 NPC65650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1819
0.2-0.3	4256
0.3-0.4	2033
0.4-0.5	517
0.5-0.6	232
0.6-0.7	94
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7973	Intermediate Similarity	NPD4137	Phase 3
0.7901	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4691	Approved
0.7867	Intermediate Similarity	NPD4747	Approved
0.7792	Intermediate Similarity	NPD5733	Approved
0.7738	Intermediate Similarity	NPD7521	Approved
0.7738	Intermediate Similarity	NPD7334	Approved
0.7738	Intermediate Similarity	NPD5330	Approved
0.7738	Intermediate Similarity	NPD7146	Approved
0.7738	Intermediate Similarity	NPD6409	Approved
0.7738	Intermediate Similarity	NPD6684	Approved
0.7619	Intermediate Similarity	NPD1694	Approved
0.7564	Intermediate Similarity	NPD4687	Approved
0.7564	Intermediate Similarity	NPD4058	Approved
0.7558	Intermediate Similarity	NPD6672	Approved
0.7558	Intermediate Similarity	NPD6903	Approved
0.7558	Intermediate Similarity	NPD5737	Approved
0.7558	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5276	Approved
0.75	Intermediate Similarity	NPD5693	Phase 1
0.7468	Intermediate Similarity	NPD8039	Approved
0.7368	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD287	Approved
0.7297	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD6904	Approved
0.7241	Intermediate Similarity	NPD3573	Approved
0.7159	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6098	Approved
0.7111	Intermediate Similarity	NPD6050	Approved
0.7111	Intermediate Similarity	NPD7515	Phase 2
0.7065	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD5207	Approved
0.6941	Remote Similarity	NPD8028	Phase 2
0.6932	Remote Similarity	NPD4623	Approved
0.6932	Remote Similarity	NPD4519	Discontinued
0.6923	Remote Similarity	NPD5694	Approved
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD7902	Approved
0.6915	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD3666	Approved
0.6897	Remote Similarity	NPD3133	Approved
0.6889	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD4223	Phase 3
0.686	Remote Similarity	NPD4221	Approved
0.6848	Remote Similarity	NPD6399	Phase 3
0.6842	Remote Similarity	NPD7638	Approved
0.6824	Remote Similarity	NPD4695	Discontinued
0.6818	Remote Similarity	NPD5329	Approved
0.6809	Remote Similarity	NPD7732	Phase 3
0.68	Remote Similarity	NPD4194	Approved
0.68	Remote Similarity	NPD4191	Approved
0.68	Remote Similarity	NPD4192	Approved
0.68	Remote Similarity	NPD4193	Approved
0.6782	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6001	Approved
0.6771	Remote Similarity	NPD7639	Approved
0.6771	Remote Similarity	NPD7640	Approved
0.6742	Remote Similarity	NPD3618	Phase 1
0.6739	Remote Similarity	NPD5284	Approved
0.6739	Remote Similarity	NPD5281	Approved
0.6705	Remote Similarity	NPD4786	Approved
0.6705	Remote Similarity	NPD4197	Approved
0.6703	Remote Similarity	NPD5328	Approved
0.6703	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.663	Remote Similarity	NPD5785	Approved
0.6588	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3617	Approved
0.6559	Remote Similarity	NPD6079	Approved
0.6556	Remote Similarity	NPD4693	Phase 3
0.6556	Remote Similarity	NPD5279	Phase 3
0.6556	Remote Similarity	NPD4689	Approved
0.6556	Remote Similarity	NPD5690	Phase 2
0.6556	Remote Similarity	NPD4138	Approved
0.6556	Remote Similarity	NPD5280	Approved
0.6556	Remote Similarity	NPD4690	Approved
0.6556	Remote Similarity	NPD5205	Approved
0.6556	Remote Similarity	NPD4688	Approved
0.6556	Remote Similarity	NPD4694	Approved
0.6538	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5654	Approved
0.6522	Remote Similarity	NPD4753	Phase 2
0.6517	Remote Similarity	NPD3668	Phase 3
0.6517	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6686	Approved
0.6458	Remote Similarity	NPD7614	Phase 1
0.6456	Remote Similarity	NPD7331	Phase 2
0.6449	Remote Similarity	NPD7115	Discovery
0.6436	Remote Similarity	NPD6402	Approved
0.6436	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD7128	Approved
0.6436	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6404	Discontinued
0.64	Remote Similarity	NPD6052	Approved
0.6392	Remote Similarity	NPD5959	Approved
0.6374	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD4202	Approved
0.6311	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.6277	Remote Similarity	NPD6698	Approved
0.6277	Remote Similarity	NPD46	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD5697	Approved
0.6214	Remote Similarity	NPD6614	Approved
0.6214	Remote Similarity	NPD5701	Approved
0.6214	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD6883	Approved
0.619	Remote Similarity	NPD7102	Approved
0.619	Remote Similarity	NPD7290	Approved
0.6186	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5210	Approved
0.6154	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD5779	Approved
0.6146	Remote Similarity	NPD5778	Approved
0.6139	Remote Similarity	NPD7632	Discontinued
0.6136	Remote Similarity	NPD4195	Approved
0.6132	Remote Similarity	NPD6617	Approved
0.6132	Remote Similarity	NPD8130	Phase 1
0.6132	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6650	Approved
0.6132	Remote Similarity	NPD6847	Approved
0.6132	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD6869	Approved
0.6125	Remote Similarity	NPD7341	Phase 2
0.6122	Remote Similarity	NPD5221	Approved
0.6122	Remote Similarity	NPD4697	Phase 3
0.6122	Remote Similarity	NPD5222	Approved
0.6122	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6927	Phase 3
0.6105	Remote Similarity	NPD4096	Approved
0.6095	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6012	Approved
0.6095	Remote Similarity	NPD6013	Approved
0.6095	Remote Similarity	NPD6014	Approved
0.6092	Remote Similarity	NPD4756	Discovery
0.6087	Remote Similarity	NPD5363	Approved
0.6087	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8297	Approved
0.6075	Remote Similarity	NPD6053	Discontinued
0.6075	Remote Similarity	NPD6882	Approved
0.6061	Remote Similarity	NPD4755	Approved
0.6061	Remote Similarity	NPD5173	Approved
0.6058	Remote Similarity	NPD6412	Phase 2
0.6049	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5362	Discontinued
0.6044	Remote Similarity	NPD4788	Approved
0.6042	Remote Similarity	NPD7637	Suspended
0.6038	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.602	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6858	Approved
0.6019	Remote Similarity	NPD7094	Approved
0.6	Remote Similarity	NPD4692	Approved
0.6	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.598	Remote Similarity	NPD5211	Phase 2
0.5979	Remote Similarity	NPD5133	Approved
0.5979	Remote Similarity	NPD7631	Approved
0.5941	Remote Similarity	NPD4700	Approved
0.5941	Remote Similarity	NPD5286	Approved
0.5941	Remote Similarity	NPD5285	Approved
0.5941	Remote Similarity	NPD4696	Approved
0.5934	Remote Similarity	NPD4270	Approved
0.5934	Remote Similarity	NPD4269	Approved
0.5914	Remote Similarity	NPD1696	Phase 3
0.5909	Remote Similarity	NPD6868	Approved
0.59	Remote Similarity	NPD3495	Discontinued
0.5895	Remote Similarity	NPD4518	Approved
0.5889	Remote Similarity	NPD4252	Approved
0.5882	Remote Similarity	NPD5777	Approved
0.5882	Remote Similarity	NPD5223	Approved
0.5876	Remote Similarity	NPD7609	Phase 3
0.5876	Remote Similarity	NPD8034	Phase 2
0.5876	Remote Similarity	NPD8035	Phase 2
0.5872	Remote Similarity	NPD4632	Approved
0.587	Remote Similarity	NPD7154	Phase 3
0.5865	Remote Similarity	NPD5141	Approved
0.5862	Remote Similarity	NPD8264	Approved
0.5851	Remote Similarity	NPD5786	Approved
0.5825	Remote Similarity	NPD5225	Approved
0.5825	Remote Similarity	NPD5226	Approved
0.5825	Remote Similarity	NPD4633	Approved
0.5825	Remote Similarity	NPD5224	Approved
0.5824	Remote Similarity	NPD5369	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