NPASS Compound

Structure

NPC109576 OpenBabel07101718302D 23 24 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 -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 1 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 1 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 1 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 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 14 19 1 1 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.782
LogD:	2.737
LogS:	-3.637
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	4.219
Fsp3:	0.7
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:	-4.971
MDCK Permeability:	2.642547588038724e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.334
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.636
Plasma Protein Binding (PPB):	88.95818328857422%
Volume Distribution (VD):	0.378
Pgp-substrate:	11.23194408416748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.642
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.309
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	2.343
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.274
Skin Sensitization:	0.969
Carcinogencity:	0.601
Eye Corrosion:	0.956
Eye Irritation:	0.819
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC109576

Natural Product ID:	NPC109576
*Common Name:**	2-Oxocleroda-3,13E-Dien-15-Oic Acid
IUPAC Name:	(E)-5-[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:	2-oxokolavenic acid
Standard InCHIKey:	SLMFLTPPPXRYHP-HZCFSAROSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13(10-18(22)23)6-8-19(4)14(2)7-9-20(5)15(3)11-16(21)12-17(19)20/h10-11,14,17H,6-9,12H2,1-5H3,(H,22,23)/b13-10+/t14-,17-,19+,20+/m0/s1
SMILES:	C/C(=CC(=O)O)/CC[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CC(=O)C=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496046
PubChem CID:	12000609
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
NPO2430	Detarium microcarpum	Species	Fabaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16724838]
NPO2430	Detarium microcarpum	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Activity	=	1.0	ug	PMID[493463]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	Activity	>	100.0	ug	PMID[493463]

☑ 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 NPC109576 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	1395
0.2-0.3	7664
0.3-0.4	15557
0.4-0.5	8492
0.5-0.6	6028
0.6-0.7	2737
0.7-0.8	570
0.8-0.85	72
0.85-0.9	15
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180015
1.0	High Similarity	NPC130016
1.0	High Similarity	NPC56747
0.971	High Similarity	NPC476346
0.9559	High Similarity	NPC133253
0.9275	High Similarity	NPC21944
0.9028	High Similarity	NPC19907
0.8889	High Similarity	NPC65650
0.8824	High Similarity	NPC242945
0.8824	High Similarity	NPC259156
0.8816	High Similarity	NPC472867
0.8816	High Similarity	NPC142253
0.8816	High Similarity	NPC3511
0.8816	High Similarity	NPC472239
0.8767	High Similarity	NPC180886
0.8649	High Similarity	NPC97377
0.863	High Similarity	NPC469803
0.859	High Similarity	NPC87552
0.8571	High Similarity	NPC469806
0.8571	High Similarity	NPC469799
0.8571	High Similarity	NPC469804
0.8571	High Similarity	NPC469805
0.8553	High Similarity	NPC469798
0.8553	High Similarity	NPC469797
0.8493	Intermediate Similarity	NPC20025
0.8481	Intermediate Similarity	NPC8571
0.8462	Intermediate Similarity	NPC3856
0.8462	Intermediate Similarity	NPC49019
0.8462	Intermediate Similarity	NPC279639
0.8406	Intermediate Similarity	NPC107258
0.84	Intermediate Similarity	NPC165711
0.84	Intermediate Similarity	NPC61952
0.8378	Intermediate Similarity	NPC476795
0.8358	Intermediate Similarity	NPC127582
0.8354	Intermediate Similarity	NPC181743
0.8354	Intermediate Similarity	NPC16287
0.8354	Intermediate Similarity	NPC178025
0.831	Intermediate Similarity	NPC260474
0.831	Intermediate Similarity	NPC188292
0.8289	Intermediate Similarity	NPC471409
0.8289	Intermediate Similarity	NPC198240
0.8289	Intermediate Similarity	NPC74410
0.8289	Intermediate Similarity	NPC275494
0.8289	Intermediate Similarity	NPC179028
0.8261	Intermediate Similarity	NPC475124
0.8261	Intermediate Similarity	NPC285371
0.825	Intermediate Similarity	NPC60350
0.8228	Intermediate Similarity	NPC97913
0.8219	Intermediate Similarity	NPC160817
0.8209	Intermediate Similarity	NPC276764
0.8209	Intermediate Similarity	NPC472304
0.8205	Intermediate Similarity	NPC471898
0.8205	Intermediate Similarity	NPC278459
0.8205	Intermediate Similarity	NPC477372
0.8194	Intermediate Similarity	NPC139397
0.8171	Intermediate Similarity	NPC72397
0.8171	Intermediate Similarity	NPC48107
0.8158	Intermediate Similarity	NPC257666
0.8158	Intermediate Similarity	NPC472300
0.8158	Intermediate Similarity	NPC266193
0.8143	Intermediate Similarity	NPC251118
0.8125	Intermediate Similarity	NPC164577
0.8125	Intermediate Similarity	NPC472865
0.8108	Intermediate Similarity	NPC35656
0.8101	Intermediate Similarity	NPC320514
0.8101	Intermediate Similarity	NPC268122
0.8082	Intermediate Similarity	NPC307176
0.8082	Intermediate Similarity	NPC2634
0.8082	Intermediate Similarity	NPC260040
0.8082	Intermediate Similarity	NPC265782
0.8082	Intermediate Similarity	NPC251929
0.8077	Intermediate Similarity	NPC26139
0.8072	Intermediate Similarity	NPC36668
0.8072	Intermediate Similarity	NPC118011
0.806	Intermediate Similarity	NPC56905
0.806	Intermediate Similarity	NPC27610
0.8056	Intermediate Similarity	NPC87141
0.8056	Intermediate Similarity	NPC155198
0.8056	Intermediate Similarity	NPC310992
0.8049	Intermediate Similarity	NPC476293
0.8049	Intermediate Similarity	NPC136948
0.8049	Intermediate Similarity	NPC476409
0.8028	Intermediate Similarity	NPC255781
0.8026	Intermediate Similarity	NPC472305
0.8026	Intermediate Similarity	NPC151622
0.8026	Intermediate Similarity	NPC7629
0.8026	Intermediate Similarity	NPC263582
0.8026	Intermediate Similarity	NPC1254
0.8	Intermediate Similarity	NPC476046
0.8	Intermediate Similarity	NPC41539
0.8	Intermediate Similarity	NPC251970
0.8	Intermediate Similarity	NPC241854
0.8	Intermediate Similarity	NPC118423
0.8	Intermediate Similarity	NPC469662
0.7973	Intermediate Similarity	NPC54123
0.7973	Intermediate Similarity	NPC190035
0.7971	Intermediate Similarity	NPC60565
0.7949	Intermediate Similarity	NPC308038
0.7949	Intermediate Similarity	NPC477371
0.7945	Intermediate Similarity	NPC256846
0.7927	Intermediate Similarity	NPC472869
0.7922	Intermediate Similarity	NPC34110
0.7922	Intermediate Similarity	NPC91665
0.7901	Intermediate Similarity	NPC96095
0.7901	Intermediate Similarity	NPC248758
0.7901	Intermediate Similarity	NPC19849
0.7901	Intermediate Similarity	NPC472864
0.7895	Intermediate Similarity	NPC279666
0.7895	Intermediate Similarity	NPC192540
0.7875	Intermediate Similarity	NPC302661
0.7875	Intermediate Similarity	NPC238991
0.7867	Intermediate Similarity	NPC474228
0.7867	Intermediate Similarity	NPC303613
0.7867	Intermediate Similarity	NPC247586
0.7857	Intermediate Similarity	NPC288253
0.7857	Intermediate Similarity	NPC262043
0.7857	Intermediate Similarity	NPC5509
0.7857	Intermediate Similarity	NPC197238
0.7857	Intermediate Similarity	NPC202118
0.7848	Intermediate Similarity	NPC271104
0.7838	Intermediate Similarity	NPC35734
0.7838	Intermediate Similarity	NPC159577
0.7838	Intermediate Similarity	NPC282593
0.7831	Intermediate Similarity	NPC181327
0.7821	Intermediate Similarity	NPC475994
0.7821	Intermediate Similarity	NPC239098
0.7821	Intermediate Similarity	NPC62336
0.7821	Intermediate Similarity	NPC321514
0.7821	Intermediate Similarity	NPC189485
0.7805	Intermediate Similarity	NPC476426
0.7805	Intermediate Similarity	NPC472931
0.7805	Intermediate Similarity	NPC29447
0.7805	Intermediate Similarity	NPC474537
0.7805	Intermediate Similarity	NPC472940
0.7805	Intermediate Similarity	NPC11711
0.7805	Intermediate Similarity	NPC189311
0.7792	Intermediate Similarity	NPC309399
0.7792	Intermediate Similarity	NPC69143
0.7792	Intermediate Similarity	NPC40353
0.7791	Intermediate Similarity	NPC469939
0.7791	Intermediate Similarity	NPC242069
0.7778	Intermediate Similarity	NPC474976
0.7778	Intermediate Similarity	NPC168188
0.7778	Intermediate Similarity	NPC102197
0.7778	Intermediate Similarity	NPC474790
0.7778	Intermediate Similarity	NPC470015
0.7778	Intermediate Similarity	NPC105803
0.7778	Intermediate Similarity	NPC81907
0.7763	Intermediate Similarity	NPC161923
0.7763	Intermediate Similarity	NPC103958
0.7763	Intermediate Similarity	NPC183503
0.7763	Intermediate Similarity	NPC213223
0.7763	Intermediate Similarity	NPC301065
0.7763	Intermediate Similarity	NPC283908
0.775	Intermediate Similarity	NPC38350
0.775	Intermediate Similarity	NPC40228
0.775	Intermediate Similarity	NPC201912
0.775	Intermediate Similarity	NPC162632
0.775	Intermediate Similarity	NPC274050
0.775	Intermediate Similarity	NPC147066
0.775	Intermediate Similarity	NPC90055
0.775	Intermediate Similarity	NPC263272
0.775	Intermediate Similarity	NPC475833
0.775	Intermediate Similarity	NPC4166
0.775	Intermediate Similarity	NPC267691
0.775	Intermediate Similarity	NPC226068
0.7746	Intermediate Similarity	NPC6697
0.7746	Intermediate Similarity	NPC212210
0.7746	Intermediate Similarity	NPC150162
0.7738	Intermediate Similarity	NPC472870
0.7738	Intermediate Similarity	NPC117122
0.7733	Intermediate Similarity	NPC115023
0.7733	Intermediate Similarity	NPC84790
0.7733	Intermediate Similarity	NPC474562
0.7722	Intermediate Similarity	NPC27817
0.7722	Intermediate Similarity	NPC170394
0.7722	Intermediate Similarity	NPC192329
0.7722	Intermediate Similarity	NPC231431
0.7714	Intermediate Similarity	NPC329416
0.7714	Intermediate Similarity	NPC317025
0.7714	Intermediate Similarity	NPC317177
0.7714	Intermediate Similarity	NPC213152
0.7714	Intermediate Similarity	NPC326645
0.7711	Intermediate Similarity	NPC194417
0.7711	Intermediate Similarity	NPC186975
0.7711	Intermediate Similarity	NPC322159
0.7711	Intermediate Similarity	NPC82979
0.7711	Intermediate Similarity	NPC473226
0.7711	Intermediate Similarity	NPC168248
0.7711	Intermediate Similarity	NPC220478
0.7703	Intermediate Similarity	NPC286814
0.7692	Intermediate Similarity	NPC107039
0.7692	Intermediate Similarity	NPC132542
0.7692	Intermediate Similarity	NPC471899
0.7692	Intermediate Similarity	NPC471897
0.7692	Intermediate Similarity	NPC74995
0.7683	Intermediate Similarity	NPC165064
0.7683	Intermediate Similarity	NPC476412
0.7674	Intermediate Similarity	NPC474018
0.7674	Intermediate Similarity	NPC473986

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 NPC109576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1806
0.2-0.3	4270
0.3-0.4	2054
0.4-0.5	484
0.5-0.6	259
0.6-0.7	106
0.7-0.8	26
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
0.8194	Intermediate Similarity	NPD4137	Phase 3
0.8082	Intermediate Similarity	NPD4747	Approved
0.8082	Intermediate Similarity	NPD4691	Approved
0.7763	Intermediate Similarity	NPD4687	Approved
0.7763	Intermediate Similarity	NPD5733	Approved
0.7763	Intermediate Similarity	NPD4058	Approved
0.7733	Intermediate Similarity	NPD5276	Approved
0.7714	Intermediate Similarity	NPD4193	Approved
0.7714	Intermediate Similarity	NPD4192	Approved
0.7714	Intermediate Similarity	NPD4191	Approved
0.7714	Intermediate Similarity	NPD4194	Approved
0.7711	Intermediate Similarity	NPD4519	Discontinued
0.7711	Intermediate Similarity	NPD4623	Approved
0.7568	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD287	Approved
0.7439	Intermediate Similarity	NPD4223	Phase 3
0.7439	Intermediate Similarity	NPD4221	Approved
0.7407	Intermediate Similarity	NPD4695	Discontinued
0.7294	Intermediate Similarity	NPD7146	Approved
0.7294	Intermediate Similarity	NPD6409	Approved
0.7294	Intermediate Similarity	NPD6684	Approved
0.7294	Intermediate Similarity	NPD5330	Approved
0.7294	Intermediate Similarity	NPD7521	Approved
0.7294	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD5284	Approved
0.7273	Intermediate Similarity	NPD5281	Approved
0.7273	Intermediate Similarity	NPD7515	Phase 2
0.7262	Intermediate Similarity	NPD3665	Phase 1
0.7262	Intermediate Similarity	NPD3133	Approved
0.7262	Intermediate Similarity	NPD3666	Approved
0.7262	Intermediate Similarity	NPD4197	Approved
0.7241	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3573	Approved
0.7176	Intermediate Similarity	NPD5329	Approved
0.716	Intermediate Similarity	NPD3617	Approved
0.7126	Intermediate Similarity	NPD5737	Approved
0.7126	Intermediate Similarity	NPD6903	Approved
0.7126	Intermediate Similarity	NPD6672	Approved
0.7126	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5208	Approved
0.7111	Intermediate Similarity	NPD7748	Approved
0.7093	Intermediate Similarity	NPD4689	Approved
0.7093	Intermediate Similarity	NPD4688	Approved
0.7093	Intermediate Similarity	NPD4694	Approved
0.7093	Intermediate Similarity	NPD4693	Phase 3
0.7093	Intermediate Similarity	NPD4690	Approved
0.7093	Intermediate Similarity	NPD5690	Phase 2
0.7093	Intermediate Similarity	NPD3618	Phase 1
0.7093	Intermediate Similarity	NPD4138	Approved
0.7093	Intermediate Similarity	NPD5280	Approved
0.7093	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD5693	Phase 1
0.7045	Intermediate Similarity	NPD6673	Approved
0.7045	Intermediate Similarity	NPD6080	Approved
0.7045	Intermediate Similarity	NPD6904	Approved
0.7033	Intermediate Similarity	NPD5695	Phase 3
0.7024	Intermediate Similarity	NPD3667	Approved
0.6977	Remote Similarity	NPD1694	Approved
0.6966	Remote Similarity	NPD5207	Approved
0.6966	Remote Similarity	NPD5692	Phase 3
0.6951	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6404	Discontinued
0.6905	Remote Similarity	NPD8028	Phase 2
0.6897	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5279	Phase 3
0.6897	Remote Similarity	NPD6098	Approved
0.6889	Remote Similarity	NPD6050	Approved
0.6889	Remote Similarity	NPD5694	Approved
0.6882	Remote Similarity	NPD6083	Phase 2
0.6882	Remote Similarity	NPD6084	Phase 2
0.6882	Remote Similarity	NPD7902	Approved
0.686	Remote Similarity	NPD4786	Approved
0.6854	Remote Similarity	NPD4753	Phase 2
0.6854	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD7331	Phase 2
0.6813	Remote Similarity	NPD6399	Phase 3
0.6809	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD7614	Phase 1
0.6739	Remote Similarity	NPD7900	Approved
0.6739	Remote Similarity	NPD6001	Approved
0.6739	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3668	Phase 3
0.663	Remote Similarity	NPD4202	Approved
0.6593	Remote Similarity	NPD4096	Approved
0.6585	Remote Similarity	NPD8039	Approved
0.6562	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD7640	Approved
0.6512	Remote Similarity	NPD4692	Approved
0.6512	Remote Similarity	NPD4139	Approved
0.6494	Remote Similarity	NPD7341	Phase 2
0.6489	Remote Similarity	NPD5210	Approved
0.6489	Remote Similarity	NPD5654	Approved
0.6489	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD7638	Approved
0.6452	Remote Similarity	NPD5133	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD4756	Discovery
0.6421	Remote Similarity	NPD5222	Approved
0.6421	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5221	Approved
0.6421	Remote Similarity	NPD4697	Phase 3
0.6421	Remote Similarity	NPD7732	Phase 3
0.6413	Remote Similarity	NPD5785	Approved
0.6404	Remote Similarity	NPD1696	Phase 3
0.6404	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD6675	Approved
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.6395	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4518	Approved
0.6364	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5959	Approved
0.6354	Remote Similarity	NPD5173	Approved
0.6354	Remote Similarity	NPD4755	Approved
0.6337	Remote Similarity	NPD5697	Approved
0.6337	Remote Similarity	NPD5701	Approved
0.6301	Remote Similarity	NPD4219	Approved
0.63	Remote Similarity	NPD5141	Approved
0.6292	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4225	Approved
0.6277	Remote Similarity	NPD5778	Approved
0.6277	Remote Similarity	NPD5779	Approved
0.6275	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD6899	Approved
0.6275	Remote Similarity	NPD6011	Approved
0.6275	Remote Similarity	NPD6881	Approved
0.6262	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.6224	Remote Similarity	NPD5286	Approved
0.6224	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD4696	Approved
0.6222	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6013	Approved
0.6214	Remote Similarity	NPD6014	Approved
0.6214	Remote Similarity	NPD6012	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.6211	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4252	Approved
0.6203	Remote Similarity	NPD4224	Phase 2
0.62	Remote Similarity	NPD6052	Approved
0.619	Remote Similarity	NPD8264	Approved
0.618	Remote Similarity	NPD5362	Discontinued
0.618	Remote Similarity	NPD4788	Approved
0.617	Remote Similarity	NPD7637	Suspended
0.617	Remote Similarity	NPD6411	Approved
0.6164	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6146	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6049	Phase 2
0.6117	Remote Similarity	NPD6686	Approved
0.61	Remote Similarity	NPD5091	Approved
0.61	Remote Similarity	NPD4633	Approved
0.61	Remote Similarity	NPD5225	Approved
0.61	Remote Similarity	NPD5226	Approved
0.61	Remote Similarity	NPD5224	Approved
0.6095	Remote Similarity	NPD6869	Approved
0.6095	Remote Similarity	NPD6650	Approved
0.6095	Remote Similarity	NPD6617	Approved
0.6095	Remote Similarity	NPD8130	Phase 1
0.6095	Remote Similarity	NPD6649	Approved
0.6095	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6008	Approved
0.6067	Remote Similarity	NPD5209	Approved
0.6044	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4754	Approved
0.604	Remote Similarity	NPD5174	Approved
0.604	Remote Similarity	NPD5175	Approved
0.6038	Remote Similarity	NPD6882	Approved
0.6038	Remote Similarity	NPD8297	Approved
0.6026	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4243	Approved
0.602	Remote Similarity	NPD3495	Discontinued
0.6019	Remote Similarity	NPD6614	Approved
0.6019	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4220	Pre-registration
0.6	Remote Similarity	NPD7154	Phase 3
0.5981	Remote Similarity	NPD4632	Approved
0.5978	Remote Similarity	NPD5786	Approved
0.5957	Remote Similarity	NPD6101	Approved
0.5957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6051	Approved
0.5941	Remote Similarity	NPD7632	Discontinued
0.5938	Remote Similarity	NPD7631	Approved
0.593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4768	Approved
0.5922	Remote Similarity	NPD4767	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