NPASS Compound

Structure

CID30321 OpenBabel06191715362D 24 26 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 4.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.8660 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 2.5981 -1.5000 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 2.5981 1.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 21 2 0 0 0 0 12 19 1 0 0 0 0 12 20 1 1 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	350.785
LogP:	4.452
LogD:	2.848
LogS:	-4.176
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	3.835
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.825292747525964e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.822
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	99.90025329589844%
Volume Distribution (VD):	1.97
Pgp-substrate:	2.1761529445648193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.482
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	3.223
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.642
Drug-inuced Liver Injury (DILI):	0.19
AMES Toxicity:	0.373
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.516
Skin Sensitization:	0.848
Carcinogencity:	0.722
Eye Corrosion:	0.003
Eye Irritation:	0.843
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC30321

Natural Product ID:	NPC30321
*Common Name:**	OUFALIMUAGMGPU-YUNKPMOVSA-N
IUPAC Name:	n.a.
Synonyms:	7-Ketoroyleanone
Standard InCHIKey:	OUFALIMUAGMGPU-YUNKPMOVSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-10(2)13-16(22)14-11(21)9-12-19(3,4)7-6-8-20(12,5)15(14)18(24)17(13)23/h10,12,23H,6-9H2,1-5H3/t12-,20-/m0/s1
SMILES:	O=C1C[C@H]2C(C)(C)CCC[C@@]2(C2=C1C(=O)C(=C(C2=O)O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813342
PubChem CID:	NA
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
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	roots	Santa Maria, South Brazil	2007-Dec	PMID[21775156]
NPO997	Peltodon longipes	Species	Lamiaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	30100.0	nM	PMID[456015]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	65800.0	nM	PMID[456015]

☑ 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 NPC30321 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	184
0.1-0.2	1456
0.2-0.3	6757
0.3-0.4	16020
0.4-0.5	9073
0.5-0.6	6105
0.6-0.7	2472
0.7-0.8	563
0.8-0.85	45
0.85-0.9	17
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC92080
0.9342	High Similarity	NPC55869
0.9315	High Similarity	NPC175079
0.9211	High Similarity	NPC108955
0.9079	High Similarity	NPC192329
0.8947	High Similarity	NPC476808
0.8875	High Similarity	NPC8518
0.8875	High Similarity	NPC132228
0.8875	High Similarity	NPC263997
0.8861	High Similarity	NPC105803
0.8846	High Similarity	NPC225515
0.8734	High Similarity	NPC103486
0.8718	High Similarity	NPC18955
0.8659	High Similarity	NPC272039
0.8659	High Similarity	NPC220930
0.8642	High Similarity	NPC6185
0.8642	High Similarity	NPC241512
0.8642	High Similarity	NPC474680
0.8625	High Similarity	NPC53733
0.859	High Similarity	NPC27817
0.8554	High Similarity	NPC307298
0.8462	Intermediate Similarity	NPC189485
0.8452	Intermediate Similarity	NPC68148
0.8452	Intermediate Similarity	NPC112454
0.8452	Intermediate Similarity	NPC65615
0.8442	Intermediate Similarity	NPC1254
0.8375	Intermediate Similarity	NPC474085
0.8375	Intermediate Similarity	NPC472684
0.8375	Intermediate Similarity	NPC44963
0.8354	Intermediate Similarity	NPC475681
0.8353	Intermediate Similarity	NPC113393
0.8256	Intermediate Similarity	NPC174167
0.8256	Intermediate Similarity	NPC470036
0.825	Intermediate Similarity	NPC2482
0.8235	Intermediate Similarity	NPC474918
0.8228	Intermediate Similarity	NPC74410
0.8205	Intermediate Similarity	NPC110725
0.8205	Intermediate Similarity	NPC180886
0.8193	Intermediate Similarity	NPC90287
0.8193	Intermediate Similarity	NPC33663
0.8182	Intermediate Similarity	NPC777
0.8171	Intermediate Similarity	NPC168188
0.8171	Intermediate Similarity	NPC470015
0.8171	Intermediate Similarity	NPC258985
0.8161	Intermediate Similarity	NPC263780
0.8161	Intermediate Similarity	NPC211230
0.8161	Intermediate Similarity	NPC271652
0.8148	Intermediate Similarity	NPC99308
0.8148	Intermediate Similarity	NPC121984
0.8148	Intermediate Similarity	NPC470034
0.8148	Intermediate Similarity	NPC116797
0.8148	Intermediate Similarity	NPC189237
0.8148	Intermediate Similarity	NPC278459
0.8148	Intermediate Similarity	NPC475863
0.814	Intermediate Similarity	NPC474209
0.814	Intermediate Similarity	NPC475823
0.8118	Intermediate Similarity	NPC230387
0.8101	Intermediate Similarity	NPC476811
0.8101	Intermediate Similarity	NPC165711
0.8095	Intermediate Similarity	NPC94666
0.8095	Intermediate Similarity	NPC229717
0.809	Intermediate Similarity	NPC272411
0.8072	Intermediate Similarity	NPC144258
0.8072	Intermediate Similarity	NPC237712
0.8068	Intermediate Similarity	NPC23170
0.8068	Intermediate Similarity	NPC474882
0.8068	Intermediate Similarity	NPC474328
0.8046	Intermediate Similarity	NPC99380
0.8025	Intermediate Similarity	NPC476809
0.8025	Intermediate Similarity	NPC26139
0.8025	Intermediate Similarity	NPC287063
0.8	Intermediate Similarity	NPC471409
0.8	Intermediate Similarity	NPC23778
0.8	Intermediate Similarity	NPC275494
0.7978	Intermediate Similarity	NPC147232
0.7976	Intermediate Similarity	NPC133652
0.7976	Intermediate Similarity	NPC123319
0.7976	Intermediate Similarity	NPC469993
0.7976	Intermediate Similarity	NPC473038
0.7976	Intermediate Similarity	NPC311702
0.7976	Intermediate Similarity	NPC94531
0.7976	Intermediate Similarity	NPC32037
0.7975	Intermediate Similarity	NPC470525
0.7952	Intermediate Similarity	NPC49019
0.7949	Intermediate Similarity	NPC470299
0.7931	Intermediate Similarity	NPC129913
0.7931	Intermediate Similarity	NPC252737
0.7927	Intermediate Similarity	NPC471898
0.7922	Intermediate Similarity	NPC144627
0.7907	Intermediate Similarity	NPC475001
0.7907	Intermediate Similarity	NPC53454
0.7907	Intermediate Similarity	NPC185059
0.7907	Intermediate Similarity	NPC58271
0.7901	Intermediate Similarity	NPC472490
0.7882	Intermediate Similarity	NPC327115
0.7875	Intermediate Similarity	NPC266193
0.7875	Intermediate Similarity	NPC257666
0.7865	Intermediate Similarity	NPC160413
0.7857	Intermediate Similarity	NPC473246
0.7857	Intermediate Similarity	NPC209882
0.7857	Intermediate Similarity	NPC96095
0.7841	Intermediate Similarity	NPC248913
0.7831	Intermediate Similarity	NPC193347
0.7831	Intermediate Similarity	NPC260956
0.7831	Intermediate Similarity	NPC469325
0.7816	Intermediate Similarity	NPC326627
0.7816	Intermediate Similarity	NPC310010
0.7805	Intermediate Similarity	NPC469637
0.7791	Intermediate Similarity	NPC470523
0.7791	Intermediate Similarity	NPC99909
0.7765	Intermediate Similarity	NPC474537
0.7765	Intermediate Similarity	NPC197823
0.7765	Intermediate Similarity	NPC469948
0.775	Intermediate Similarity	NPC69143
0.775	Intermediate Similarity	NPC263582
0.775	Intermediate Similarity	NPC26504
0.775	Intermediate Similarity	NPC309399
0.7738	Intermediate Similarity	NPC291999
0.7738	Intermediate Similarity	NPC472492
0.7738	Intermediate Similarity	NPC309309
0.7738	Intermediate Similarity	NPC8091
0.7711	Intermediate Similarity	NPC201912
0.7711	Intermediate Similarity	NPC473217
0.7711	Intermediate Similarity	NPC38350
0.7711	Intermediate Similarity	NPC150506
0.7711	Intermediate Similarity	NPC226068
0.7711	Intermediate Similarity	NPC477372
0.7701	Intermediate Similarity	NPC470524
0.7701	Intermediate Similarity	NPC72397
0.7701	Intermediate Similarity	NPC471722
0.7692	Intermediate Similarity	NPC84790
0.7692	Intermediate Similarity	NPC96859
0.7692	Intermediate Similarity	NPC328162
0.7692	Intermediate Similarity	NPC305483
0.7683	Intermediate Similarity	NPC474113
0.7683	Intermediate Similarity	NPC199595
0.7674	Intermediate Similarity	NPC118648
0.7674	Intermediate Similarity	NPC31564
0.7674	Intermediate Similarity	NPC472974
0.7674	Intermediate Similarity	NPC474778
0.7674	Intermediate Similarity	NPC222613
0.7674	Intermediate Similarity	NPC145879
0.7674	Intermediate Similarity	NPC472488
0.7674	Intermediate Similarity	NPC475022
0.7674	Intermediate Similarity	NPC20688
0.7674	Intermediate Similarity	NPC474732
0.7674	Intermediate Similarity	NPC72133
0.7674	Intermediate Similarity	NPC474733
0.7674	Intermediate Similarity	NPC475181
0.7674	Intermediate Similarity	NPC51014
0.7674	Intermediate Similarity	NPC56588
0.7667	Intermediate Similarity	NPC245972
0.7667	Intermediate Similarity	NPC212812
0.7667	Intermediate Similarity	NPC196485
0.7654	Intermediate Similarity	NPC197659
0.7654	Intermediate Similarity	NPC472300
0.7654	Intermediate Similarity	NPC97377
0.7647	Intermediate Similarity	NPC321187
0.7647	Intermediate Similarity	NPC85774
0.7647	Intermediate Similarity	NPC329043
0.7647	Intermediate Similarity	NPC53385
0.7647	Intermediate Similarity	NPC161423
0.7647	Intermediate Similarity	NPC214043
0.7647	Intermediate Similarity	NPC227064
0.7647	Intermediate Similarity	NPC58841
0.764	Intermediate Similarity	NPC73457
0.764	Intermediate Similarity	NPC168027
0.764	Intermediate Similarity	NPC26865
0.764	Intermediate Similarity	NPC185936
0.7625	Intermediate Similarity	NPC279666
0.7625	Intermediate Similarity	NPC192540
0.7619	Intermediate Similarity	NPC48362
0.7619	Intermediate Similarity	NPC212083
0.7619	Intermediate Similarity	NPC327969
0.7619	Intermediate Similarity	NPC73882
0.7619	Intermediate Similarity	NPC151519
0.7619	Intermediate Similarity	NPC320514
0.7619	Intermediate Similarity	NPC69101
0.7619	Intermediate Similarity	NPC251779
0.7619	Intermediate Similarity	NPC310989
0.7619	Intermediate Similarity	NPC238991
0.7619	Intermediate Similarity	NPC302661
0.7619	Intermediate Similarity	NPC321289
0.7614	Intermediate Similarity	NPC472676
0.7614	Intermediate Similarity	NPC1015
0.7614	Intermediate Similarity	NPC31985
0.7614	Intermediate Similarity	NPC477973
0.7614	Intermediate Similarity	NPC472688
0.7614	Intermediate Similarity	NPC474245
0.7609	Intermediate Similarity	NPC43747
0.7595	Intermediate Similarity	NPC247586
0.759	Intermediate Similarity	NPC279667
0.759	Intermediate Similarity	NPC472478
0.759	Intermediate Similarity	NPC37038
0.759	Intermediate Similarity	NPC474956
0.7586	Intermediate Similarity	NPC136948
0.7586	Intermediate Similarity	NPC136548
0.7586	Intermediate Similarity	NPC475740
0.7586	Intermediate Similarity	NPC58063
0.7582	Intermediate Similarity	NPC295347

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 NPC30321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2015
0.2-0.3	4129
0.3-0.4	2020
0.4-0.5	438
0.5-0.6	189
0.6-0.7	140
0.7-0.8	35
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8961	High Similarity	NPD4695	Discontinued
0.8947	High Similarity	NPD3617	Approved
0.8452	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4694	Approved
0.8095	Intermediate Similarity	NPD5280	Approved
0.8095	Intermediate Similarity	NPD5690	Phase 2
0.8072	Intermediate Similarity	NPD4197	Approved
0.7976	Intermediate Similarity	NPD5329	Approved
0.7882	Intermediate Similarity	NPD5279	Phase 3
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4753	Phase 2
0.7711	Intermediate Similarity	NPD4692	Approved
0.7711	Intermediate Similarity	NPD4139	Approved
0.7674	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7619	Intermediate Similarity	NPD3667	Approved
0.7582	Intermediate Similarity	NPD5695	Phase 3
0.7556	Intermediate Similarity	NPD5133	Approved
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD3618	Phase 1
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD4519	Discontinued
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD5281	Approved
0.7444	Intermediate Similarity	NPD5284	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD5210	Approved
0.7391	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD7341	Phase 2
0.7333	Intermediate Similarity	NPD5692	Phase 3
0.7333	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5222	Approved
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD4697	Phase 3
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7253	Intermediate Similarity	NPD6050	Approved
0.7253	Intermediate Similarity	NPD7515	Phase 2
0.7253	Intermediate Similarity	NPD5694	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD6083	Phase 2
0.7234	Intermediate Similarity	NPD5173	Approved
0.7234	Intermediate Similarity	NPD6084	Phase 2
0.7234	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD6904	Approved
0.7222	Intermediate Similarity	NPD6080	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7222	Intermediate Similarity	NPD6673	Approved
0.7215	Intermediate Similarity	NPD4137	Phase 3
0.7158	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD4096	Approved
0.7128	Intermediate Similarity	NPD7614	Phase 1
0.7125	Intermediate Similarity	NPD4747	Approved
0.7125	Intermediate Similarity	NPD4691	Approved
0.7111	Intermediate Similarity	NPD4518	Approved
0.7097	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7073	Intermediate Similarity	NPD5733	Approved
0.7073	Intermediate Similarity	NPD4687	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD4195	Approved
0.7051	Intermediate Similarity	NPD3704	Approved
0.7037	Intermediate Similarity	NPD5276	Approved
0.7021	Intermediate Similarity	NPD5654	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.6989	Remote Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD4202	Approved
0.6977	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD5091	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6932	Remote Similarity	NPD4788	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6889	Remote Similarity	NPD6098	Approved
0.6889	Remote Similarity	NPD7521	Approved
0.6875	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD5959	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6835	Remote Similarity	NPD7331	Phase 2
0.6818	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3573	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6774	Remote Similarity	NPD5207	Approved
0.6739	Remote Similarity	NPD5208	Approved
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6625	Remote Similarity	NPD4224	Phase 2
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6598	Remote Similarity	NPD7732	Phase 3
0.6593	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7900	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6526	Remote Similarity	NPD6411	Approved
0.6517	Remote Similarity	NPD8028	Phase 2
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD5135	Approved
0.6471	Remote Similarity	NPD4785	Approved
0.6471	Remote Similarity	NPD4784	Approved
0.6463	Remote Similarity	NPD5360	Phase 3
0.6463	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6081	Approved
0.6429	Remote Similarity	NPD4243	Approved
0.6415	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD5217	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD5215	Approved
0.6415	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6650	Approved
0.6404	Remote Similarity	NPD4748	Discontinued
0.64	Remote Similarity	NPD6404	Discontinued
0.6395	Remote Similarity	NPD6942	Approved
0.6395	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD6001	Approved
0.6386	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3698	Phase 2
0.6386	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD287	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6346	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4244	Approved
0.631	Remote Similarity	NPD4245	Approved
0.6296	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD4756	Discovery
0.6239	Remote Similarity	NPD5167	Approved
0.6237	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD1694	Approved
0.6235	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4758	Discontinued
0.6235	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4190	Phase 3
0.6207	Remote Similarity	NPD5275	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