NPASS Compound

Structure

NPC74410 OpenBabel07101719142D 24 25 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 3.4641 2.0000 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 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 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 -0.5000 -2.5981 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 1.7321 2.0000 0.0000 C 0 0 0 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.4641 0.0000 O 0 0 0 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 6 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	356.705
LogP:	3.969
LogD:	2.776
LogS:	-3.647
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	3.924
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.937
MDCK Permeability:	1.9483721189317293e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.9
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	97.58777618408203%
Volume Distribution (VD):	0.333
Pgp-substrate:	2.183199644088745%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.66
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	7.005
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.389
Carcinogencity:	0.729
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC74410

Natural Product ID:	NPC74410
*Common Name:**	Callicarpic Acid B
IUPAC Name:	3-[(1S,2S)-1-methyl-5,8-dioxo-6-propan-2-yl-2-prop-1-en-2-yl-3,4-dihydro-2H-naphthalen-1-yl]propanoic acid
Synonyms:	Callicarpic Acid B
Standard InCHIKey:	GPJZKLLQWSDGSG-YWZLYKJASA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-11(2)14-10-16(21)18-13(19(14)24)6-7-15(12(3)4)20(18,5)9-8-17(22)23/h10-11,15H,3,6-9H2,1-2,4-5H3,(H,22,23)/t15-,20-/m0/s1
SMILES:	CC(C)C1=CC(=O)C2=C(CC[C@@H](C(=C)C)[C@]2(C)CCC(=O)O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559707
PubChem CID:	25227580
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones

*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
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193025]
NPO17126	Callicarpa pilosissima	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	63600.0	nM	PMID[521634]

☑ 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 NPC74410 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	181
0.1-0.2	1213
0.2-0.3	6247
0.3-0.4	15450
0.4-0.5	8845
0.5-0.6	6352
0.6-0.7	3559
0.7-0.8	775
0.8-0.85	64
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC180886
0.9351	High Similarity	NPC49019
0.9342	High Similarity	NPC278459
0.9067	High Similarity	NPC165711
0.9067	High Similarity	NPC97377
0.8919	High Similarity	NPC301065
0.8875	High Similarity	NPC474537
0.8861	High Similarity	NPC105803
0.8846	High Similarity	NPC477372
0.8846	High Similarity	NPC90055
0.8846	High Similarity	NPC471898
0.8846	High Similarity	NPC55869
0.88	High Similarity	NPC476795
0.878	High Similarity	NPC72397
0.875	High Similarity	NPC96095
0.8734	High Similarity	NPC238991
0.8734	High Similarity	NPC302661
0.8718	High Similarity	NPC108955
0.8718	High Similarity	NPC26139
0.8701	High Similarity	NPC321514
0.8701	High Similarity	NPC198240
0.8701	High Similarity	NPC189485
0.8684	High Similarity	NPC309399
0.8684	High Similarity	NPC470525
0.8649	High Similarity	NPC160817
0.8642	High Similarity	NPC474680
0.8642	High Similarity	NPC29447
0.8625	High Similarity	NPC168188
0.8625	High Similarity	NPC97913
0.8625	High Similarity	NPC470015
0.8625	High Similarity	NPC102197
0.8608	High Similarity	NPC38350
0.8608	High Similarity	NPC116797
0.8608	High Similarity	NPC201912
0.859	High Similarity	NPC477371
0.859	High Similarity	NPC192329
0.8571	High Similarity	NPC61952
0.8571	High Similarity	NPC472300
0.8554	High Similarity	NPC48107
0.8553	High Similarity	NPC192540
0.8553	High Similarity	NPC279666
0.8533	High Similarity	NPC35656
0.8519	High Similarity	NPC472865
0.8519	High Similarity	NPC164577
0.85	High Similarity	NPC103486
0.85	High Similarity	NPC260956
0.85	High Similarity	NPC320514
0.85	High Similarity	NPC133391
0.8481	Intermediate Similarity	NPC271104
0.8481	Intermediate Similarity	NPC37038
0.8481	Intermediate Similarity	NPC476809
0.8471	Intermediate Similarity	NPC204341
0.8462	Intermediate Similarity	NPC471409
0.8462	Intermediate Similarity	NPC59436
0.8462	Intermediate Similarity	NPC260385
0.8462	Intermediate Similarity	NPC110094
0.8462	Intermediate Similarity	NPC275494
0.8462	Intermediate Similarity	NPC280654
0.8462	Intermediate Similarity	NPC179028
0.8452	Intermediate Similarity	NPC477973
0.8452	Intermediate Similarity	NPC262043
0.8452	Intermediate Similarity	NPC5509
0.8442	Intermediate Similarity	NPC69143
0.8434	Intermediate Similarity	NPC476409
0.8434	Intermediate Similarity	NPC136948
0.8421	Intermediate Similarity	NPC161923
0.8421	Intermediate Similarity	NPC476046
0.8421	Intermediate Similarity	NPC213223
0.8421	Intermediate Similarity	NPC103958
0.8421	Intermediate Similarity	NPC241854
0.8421	Intermediate Similarity	NPC251970
0.8421	Intermediate Similarity	NPC183503
0.8421	Intermediate Similarity	NPC283908
0.8415	Intermediate Similarity	NPC123319
0.8415	Intermediate Similarity	NPC142649
0.8415	Intermediate Similarity	NPC311702
0.8415	Intermediate Similarity	NPC94531
0.8415	Intermediate Similarity	NPC132228
0.8415	Intermediate Similarity	NPC8518
0.8415	Intermediate Similarity	NPC263997
0.8395	Intermediate Similarity	NPC83569
0.8395	Intermediate Similarity	NPC69279
0.8395	Intermediate Similarity	NPC477373
0.8375	Intermediate Similarity	NPC162632
0.8375	Intermediate Similarity	NPC274050
0.8375	Intermediate Similarity	NPC147066
0.8375	Intermediate Similarity	NPC44963
0.8375	Intermediate Similarity	NPC267691
0.8375	Intermediate Similarity	NPC327002
0.8375	Intermediate Similarity	NPC263272
0.8375	Intermediate Similarity	NPC472684
0.8354	Intermediate Similarity	NPC231431
0.8354	Intermediate Similarity	NPC196827
0.8354	Intermediate Similarity	NPC274996
0.8354	Intermediate Similarity	NPC327674
0.8354	Intermediate Similarity	NPC199595
0.8333	Intermediate Similarity	NPC266193
0.8333	Intermediate Similarity	NPC471899
0.8333	Intermediate Similarity	NPC471897
0.8333	Intermediate Similarity	NPC257666
0.8333	Intermediate Similarity	NPC473229
0.8333	Intermediate Similarity	NPC107039
0.8313	Intermediate Similarity	NPC472869
0.8312	Intermediate Similarity	NPC472327
0.8312	Intermediate Similarity	NPC476346
0.8293	Intermediate Similarity	NPC19849
0.8293	Intermediate Similarity	NPC248758
0.8293	Intermediate Similarity	NPC472864
0.8289	Intermediate Similarity	NPC180015
0.8289	Intermediate Similarity	NPC130016
0.8289	Intermediate Similarity	NPC109576
0.8289	Intermediate Similarity	NPC56747
0.8272	Intermediate Similarity	NPC69101
0.8272	Intermediate Similarity	NPC251779
0.8256	Intermediate Similarity	NPC230064
0.825	Intermediate Similarity	NPC2482
0.825	Intermediate Similarity	NPC104545
0.8235	Intermediate Similarity	NPC112454
0.8235	Intermediate Similarity	NPC214387
0.8235	Intermediate Similarity	NPC36668
0.8235	Intermediate Similarity	NPC118011
0.8228	Intermediate Similarity	NPC62336
0.8228	Intermediate Similarity	NPC30321
0.8214	Intermediate Similarity	NPC470523
0.8205	Intermediate Similarity	NPC89294
0.8205	Intermediate Similarity	NPC76966
0.8205	Intermediate Similarity	NPC92080
0.8205	Intermediate Similarity	NPC263582
0.8205	Intermediate Similarity	NPC186554
0.8193	Intermediate Similarity	NPC241512
0.8193	Intermediate Similarity	NPC189311
0.8193	Intermediate Similarity	NPC11711
0.8193	Intermediate Similarity	NPC473038
0.8193	Intermediate Similarity	NPC6185
0.8182	Intermediate Similarity	NPC306928
0.8182	Intermediate Similarity	NPC147232
0.8182	Intermediate Similarity	NPC3753
0.8182	Intermediate Similarity	NPC237591
0.8182	Intermediate Similarity	NPC171395
0.8171	Intermediate Similarity	NPC310470
0.8171	Intermediate Similarity	NPC53733
0.8171	Intermediate Similarity	NPC70834
0.8161	Intermediate Similarity	NPC263780
0.8148	Intermediate Similarity	NPC473217
0.8148	Intermediate Similarity	NPC121984
0.8148	Intermediate Similarity	NPC473420
0.8148	Intermediate Similarity	NPC221647
0.8148	Intermediate Similarity	NPC40228
0.8148	Intermediate Similarity	NPC225515
0.8148	Intermediate Similarity	NPC226068
0.8148	Intermediate Similarity	NPC189237
0.8148	Intermediate Similarity	NPC142244
0.814	Intermediate Similarity	NPC477147
0.814	Intermediate Similarity	NPC476437
0.814	Intermediate Similarity	NPC476369
0.814	Intermediate Similarity	NPC477149
0.8125	Intermediate Similarity	NPC27817
0.8125	Intermediate Similarity	NPC16394
0.8125	Intermediate Similarity	NPC472490
0.8118	Intermediate Similarity	NPC117122
0.8118	Intermediate Similarity	NPC470524
0.8118	Intermediate Similarity	NPC472870
0.8101	Intermediate Similarity	NPC212661
0.8101	Intermediate Similarity	NPC471035
0.8101	Intermediate Similarity	NPC197659
0.8095	Intermediate Similarity	NPC477478
0.8095	Intermediate Similarity	NPC186975
0.8095	Intermediate Similarity	NPC477479
0.809	Intermediate Similarity	NPC456
0.809	Intermediate Similarity	NPC472941
0.8082	Intermediate Similarity	NPC251118
0.8077	Intermediate Similarity	NPC114236
0.8077	Intermediate Similarity	NPC476844
0.8072	Intermediate Similarity	NPC209882
0.8072	Intermediate Similarity	NPC473246
0.8072	Intermediate Similarity	NPC156981
0.8052	Intermediate Similarity	NPC472813
0.8049	Intermediate Similarity	NPC193347
0.8049	Intermediate Similarity	NPC296367
0.8049	Intermediate Similarity	NPC321289
0.8049	Intermediate Similarity	NPC142253
0.8049	Intermediate Similarity	NPC3511
0.8049	Intermediate Similarity	NPC73882
0.8049	Intermediate Similarity	NPC327969
0.8046	Intermediate Similarity	NPC473986
0.8046	Intermediate Similarity	NPC233455
0.8046	Intermediate Similarity	NPC470036
0.8046	Intermediate Similarity	NPC174167
0.8046	Intermediate Similarity	NPC474018
0.8046	Intermediate Similarity	NPC158030
0.8046	Intermediate Similarity	NPC145067
0.8046	Intermediate Similarity	NPC4036
0.8046	Intermediate Similarity	NPC65120
0.8026	Intermediate Similarity	NPC235586
0.8025	Intermediate Similarity	NPC477057
0.8025	Intermediate Similarity	NPC472478
0.8025	Intermediate Similarity	NPC469637
0.8	Intermediate Similarity	NPC260474
0.8	Intermediate Similarity	NPC173089
0.8	Intermediate Similarity	NPC476253

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 NPC74410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1897
0.2-0.3	3863
0.3-0.4	2158
0.4-0.5	610
0.5-0.6	263
0.6-0.7	171
0.7-0.8	24
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
0.8481	Intermediate Similarity	NPD4695	Discontinued
0.8256	Intermediate Similarity	NPD5281	Approved
0.8256	Intermediate Similarity	NPD5284	Approved
0.8235	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5690	Phase 2
0.8049	Intermediate Similarity	NPD4223	Phase 3
0.8049	Intermediate Similarity	NPD4221	Approved
0.8046	Intermediate Similarity	NPD7515	Phase 2
0.7978	Intermediate Similarity	NPD5695	Phase 3
0.7889	Intermediate Similarity	NPD7614	Phase 1
0.7882	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4694	Approved
0.7882	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD4197	Approved
0.7857	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD3666	Approved
0.7857	Intermediate Similarity	NPD3133	Approved
0.7791	Intermediate Similarity	NPD3573	Approved
0.7778	Intermediate Similarity	NPD3617	Approved
0.7765	Intermediate Similarity	NPD5329	Approved
0.7727	Intermediate Similarity	NPD5692	Phase 3
0.7701	Intermediate Similarity	NPD6672	Approved
0.7701	Intermediate Similarity	NPD5737	Approved
0.7674	Intermediate Similarity	NPD4138	Approved
0.7674	Intermediate Similarity	NPD4688	Approved
0.7674	Intermediate Similarity	NPD6409	Approved
0.7674	Intermediate Similarity	NPD7334	Approved
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD5205	Approved
0.7674	Intermediate Similarity	NPD4623	Approved
0.7674	Intermediate Similarity	NPD5330	Approved
0.7674	Intermediate Similarity	NPD4689	Approved
0.7674	Intermediate Similarity	NPD7146	Approved
0.7674	Intermediate Similarity	NPD4690	Approved
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7674	Intermediate Similarity	NPD4519	Discontinued
0.7674	Intermediate Similarity	NPD7521	Approved
0.7674	Intermediate Similarity	NPD6684	Approved
0.7674	Intermediate Similarity	NPD4693	Phase 3
0.764	Intermediate Similarity	NPD6050	Approved
0.764	Intermediate Similarity	NPD5694	Approved
0.7619	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3667	Approved
0.7614	Intermediate Similarity	NPD6673	Approved
0.7614	Intermediate Similarity	NPD6904	Approved
0.7614	Intermediate Similarity	NPD6080	Approved
0.7614	Intermediate Similarity	NPD4753	Phase 2
0.7609	Intermediate Similarity	NPD7902	Approved
0.7609	Intermediate Similarity	NPD6083	Phase 2
0.7609	Intermediate Similarity	NPD6084	Phase 2
0.7564	Intermediate Similarity	NPD4691	Approved
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7528	Intermediate Similarity	NPD5207	Approved
0.7527	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD7331	Phase 2
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4195	Approved
0.7444	Intermediate Similarity	NPD5693	Phase 1
0.7444	Intermediate Similarity	NPD6079	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7436	Intermediate Similarity	NPD4137	Phase 3
0.7416	Intermediate Similarity	NPD5328	Approved
0.7391	Intermediate Similarity	NPD5210	Approved
0.7391	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD7341	Phase 2
0.7342	Intermediate Similarity	NPD4747	Approved
0.7333	Intermediate Similarity	NPD4096	Approved
0.7312	Intermediate Similarity	NPD7732	Phase 3
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD5222	Approved
0.7303	Intermediate Similarity	NPD4518	Approved
0.7294	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD4692	Approved
0.7284	Intermediate Similarity	NPD4058	Approved
0.7284	Intermediate Similarity	NPD4687	Approved
0.7284	Intermediate Similarity	NPD5733	Approved
0.7283	Intermediate Similarity	NPD7900	Approved
0.7283	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6098	Approved
0.7263	Intermediate Similarity	NPD6404	Discontinued
0.7253	Intermediate Similarity	NPD6411	Approved
0.725	Intermediate Similarity	NPD5276	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5654	Approved
0.7174	Intermediate Similarity	NPD4202	Approved
0.7174	Intermediate Similarity	NPD5133	Approved
0.7172	Intermediate Similarity	NPD5697	Approved
0.7159	Intermediate Similarity	NPD1694	Approved
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7105	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6011	Approved
0.71	Intermediate Similarity	NPD6881	Approved
0.71	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD6675	Approved
0.7071	Intermediate Similarity	NPD6402	Approved
0.7071	Intermediate Similarity	NPD5739	Approved
0.7071	Intermediate Similarity	NPD7128	Approved
0.7053	Intermediate Similarity	NPD5959	Approved
0.7053	Intermediate Similarity	NPD4755	Approved
0.7033	Intermediate Similarity	NPD6101	Approved
0.7033	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6014	Approved
0.703	Intermediate Similarity	NPD6013	Approved
0.703	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD287	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.6977	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7102	Approved
0.6961	Remote Similarity	NPD6883	Approved
0.6961	Remote Similarity	NPD7290	Approved
0.6941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD5091	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6932	Remote Similarity	NPD4788	Approved
0.6931	Remote Similarity	NPD7320	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6893	Remote Similarity	NPD6869	Approved
0.6893	Remote Similarity	NPD6649	Approved
0.6893	Remote Similarity	NPD6617	Approved
0.6893	Remote Similarity	NPD8130	Phase 1
0.6893	Remote Similarity	NPD6650	Approved
0.6893	Remote Similarity	NPD6847	Approved
0.6875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6863	Remote Similarity	NPD6373	Approved
0.6863	Remote Similarity	NPD6372	Approved
0.6835	Remote Similarity	NPD4224	Phase 2
0.6827	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD6882	Approved
0.6824	Remote Similarity	NPD4756	Discovery
0.6809	Remote Similarity	NPD5778	Approved
0.6809	Remote Similarity	NPD5779	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6778	Remote Similarity	NPD5363	Approved
0.6778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD4632	Approved
0.6742	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6731	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8028	Phase 2
0.67	Remote Similarity	NPD4754	Approved
0.67	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6614	Approved
0.6636	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD6274	Approved
0.6633	Remote Similarity	NPD4225	Approved
0.6627	Remote Similarity	NPD6081	Approved
0.6627	Remote Similarity	NPD4243	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6593	Remote Similarity	NPD1696	Phase 3
0.6591	Remote Similarity	NPD5368	Approved
0.6588	Remote Similarity	NPD8039	Approved
0.6575	Remote Similarity	NPD3172	Approved
0.6574	Remote Similarity	NPD6009	Approved
0.6574	Remote Similarity	NPD6317	Approved
0.6574	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD6008	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD4767	Approved
0.6538	Remote Similarity	NPD4194	Approved
0.6538	Remote Similarity	NPD4193	Approved
0.6538	Remote Similarity	NPD4191	Approved
0.6538	Remote Similarity	NPD4192	Approved
0.6526	Remote Similarity	NPD8035	Phase 2
0.6526	Remote Similarity	NPD8034	Phase 2
0.6517	Remote Similarity	NPD857	Phase 3
0.6517	Remote Similarity	NPD5369	Approved
0.6514	Remote Similarity	NPD6335	Approved
0.6514	Remote Similarity	NPD6314	Approved
0.6514	Remote Similarity	NPD6313	Approved
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3195	Phase 2
0.6486	Remote Similarity	NPD3194	Approved
0.6486	Remote Similarity	NPD3196	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