NPASS Compound

Structure

NPC301065 OpenBabel07101719512D 22 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 1.7321 1.0000 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 -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 -1.7321 -0.0000 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 -1.7321 -2.0000 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 -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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 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 0.0000 3.4641 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 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 16 18 1 0 0 0 0 17 20 1 6 0 0 0 18 20 1 6 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	344.398
LogP:	4.667
LogD:	3.535
LogS:	-4.014
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	4.286
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	2.9291302780620754e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	95.4073486328125%
Volume Distribution (VD):	0.311
Pgp-substrate:	2.128873109817505%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	3.067
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.918
Carcinogencity:	0.739
Eye Corrosion:	0.411
Eye Irritation:	0.307
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC301065

Natural Product ID:	NPC301065
*Common Name:**	Callicarpic Acid A
IUPAC Name:	3-[(1S,2S,8aR)-1-methyl-6-propan-2-yl-2-prop-1-en-2-yl-3,7,8,8a-tetrahydro-2H-naphthalen-1-yl]propanoic acid
Synonyms:	Callicarpic Acid A
Standard InCHIKey:	YJZGFOZCXWCRQH-BJLQDIEVSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)15-6-9-18-16(12-15)7-8-17(14(3)4)20(18,5)11-10-19(21)22/h7,12-13,17-18H,3,6,8-11H2,1-2,4-5H3,(H,21,22)/t17-,18-,20-/m0/s1
SMILES:	CC(C)C1=CC2=CC[C@@H](C(=C)C)[C@](C)(CCC(=O)O)[C@H]2CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL553670
PubChem CID:	25243667
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001205] Carboxylic acids

*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	=	238400.0	nM	PMID[480898]

☑ 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 NPC301065 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	187
0.1-0.2	1082
0.2-0.3	6429
0.3-0.4	16896
0.4-0.5	8923
0.5-0.6	6305
0.6-0.7	2458
0.7-0.8	372
0.8-0.85	30
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC309399
0.9155	High Similarity	NPC237591
0.9155	High Similarity	NPC306928
0.9155	High Similarity	NPC3753
0.9143	High Similarity	NPC160817
0.9054	High Similarity	NPC196827
0.9054	High Similarity	NPC274996
0.9028	High Similarity	NPC192540
0.9028	High Similarity	NPC279666
0.9028	High Similarity	NPC476844
0.8919	High Similarity	NPC74410
0.8904	High Similarity	NPC899
0.8904	High Similarity	NPC69143
0.8889	High Similarity	NPC241854
0.8889	High Similarity	NPC251970
0.8889	High Similarity	NPC161923
0.8889	High Similarity	NPC213223
0.8889	High Similarity	NPC283908
0.8889	High Similarity	NPC183503
0.8889	High Similarity	NPC476046
0.8889	High Similarity	NPC103958
0.8831	High Similarity	NPC69279
0.8831	High Similarity	NPC83569
0.8816	High Similarity	NPC142244
0.8784	High Similarity	NPC471899
0.8784	High Similarity	NPC107039
0.8784	High Similarity	NPC471897
0.8767	High Similarity	NPC476795
0.8701	High Similarity	NPC296367
0.8667	High Similarity	NPC260385
0.8667	High Similarity	NPC321514
0.8667	High Similarity	NPC4827
0.8667	High Similarity	NPC110094
0.8667	High Similarity	NPC179028
0.8667	High Similarity	NPC280654
0.8649	High Similarity	NPC180886
0.8649	High Similarity	NPC89294
0.859	High Similarity	NPC70834
0.859	High Similarity	NPC310470
0.8571	High Similarity	NPC38350
0.8571	High Similarity	NPC201912
0.8553	High Similarity	NPC327674
0.8553	High Similarity	NPC199595
0.8553	High Similarity	NPC231431
0.8553	High Similarity	NPC477371
0.8553	High Similarity	NPC16394
0.8533	High Similarity	NPC165711
0.85	High Similarity	NPC239685
0.8493	Intermediate Similarity	NPC35656
0.8462	Intermediate Similarity	NPC260956
0.8442	Intermediate Similarity	NPC37038
0.8442	Intermediate Similarity	NPC104545
0.8421	Intermediate Similarity	NPC189485
0.8354	Intermediate Similarity	NPC102197
0.8354	Intermediate Similarity	NPC49019
0.8333	Intermediate Similarity	NPC274050
0.8333	Intermediate Similarity	NPC162632
0.8333	Intermediate Similarity	NPC473420
0.8333	Intermediate Similarity	NPC147066
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC221647
0.8333	Intermediate Similarity	NPC263272
0.8333	Intermediate Similarity	NPC471898
0.8333	Intermediate Similarity	NPC327002
0.8333	Intermediate Similarity	NPC267691
0.8333	Intermediate Similarity	NPC477372
0.8312	Intermediate Similarity	NPC158846
0.8293	Intermediate Similarity	NPC72397
0.8293	Intermediate Similarity	NPC24816
0.8289	Intermediate Similarity	NPC61952
0.8289	Intermediate Similarity	NPC97377
0.8267	Intermediate Similarity	NPC201027
0.8228	Intermediate Similarity	NPC133391
0.8228	Intermediate Similarity	NPC15910
0.8228	Intermediate Similarity	NPC73882
0.8228	Intermediate Similarity	NPC69101
0.8228	Intermediate Similarity	NPC251779
0.8205	Intermediate Similarity	NPC477057
0.8205	Intermediate Similarity	NPC26139
0.8194	Intermediate Similarity	NPC290445
0.8194	Intermediate Similarity	NPC36616
0.8193	Intermediate Similarity	NPC77168
0.8193	Intermediate Similarity	NPC84271
0.8193	Intermediate Similarity	NPC102414
0.8182	Intermediate Similarity	NPC239098
0.8182	Intermediate Similarity	NPC198240
0.8182	Intermediate Similarity	NPC59436
0.8182	Intermediate Similarity	NPC169095
0.8148	Intermediate Similarity	NPC76333
0.8148	Intermediate Similarity	NPC474537
0.8143	Intermediate Similarity	NPC234767
0.8133	Intermediate Similarity	NPC166797
0.8125	Intermediate Similarity	NPC312480
0.8125	Intermediate Similarity	NPC97913
0.8125	Intermediate Similarity	NPC200752
0.8125	Intermediate Similarity	NPC477373
0.8101	Intermediate Similarity	NPC121984
0.8101	Intermediate Similarity	NPC225515
0.8095	Intermediate Similarity	NPC46281
0.8077	Intermediate Similarity	NPC474113
0.8072	Intermediate Similarity	NPC48866
0.8072	Intermediate Similarity	NPC247406
0.8052	Intermediate Similarity	NPC472300
0.8025	Intermediate Similarity	NPC164577
0.8025	Intermediate Similarity	NPC472865
0.8025	Intermediate Similarity	NPC165064
0.8025	Intermediate Similarity	NPC156981
0.8025	Intermediate Similarity	NPC96095
0.8025	Intermediate Similarity	NPC477289
0.8	Intermediate Similarity	NPC320514
0.8	Intermediate Similarity	NPC161187
0.8	Intermediate Similarity	NPC301244
0.8	Intermediate Similarity	NPC238991
0.8	Intermediate Similarity	NPC244708
0.8	Intermediate Similarity	NPC330659
0.8	Intermediate Similarity	NPC36310
0.8	Intermediate Similarity	NPC204341
0.8	Intermediate Similarity	NPC302661
0.7976	Intermediate Similarity	NPC36668
0.7976	Intermediate Similarity	NPC112454
0.7976	Intermediate Similarity	NPC95246
0.7976	Intermediate Similarity	NPC474972
0.7976	Intermediate Similarity	NPC118011
0.7976	Intermediate Similarity	NPC161751
0.7975	Intermediate Similarity	NPC271104
0.7975	Intermediate Similarity	NPC108955
0.7973	Intermediate Similarity	NPC235586
0.7973	Intermediate Similarity	NPC91369
0.7952	Intermediate Similarity	NPC71507
0.7952	Intermediate Similarity	NPC233836
0.7952	Intermediate Similarity	NPC312215
0.7952	Intermediate Similarity	NPC159046
0.7952	Intermediate Similarity	NPC187376
0.7949	Intermediate Similarity	NPC275494
0.7949	Intermediate Similarity	NPC471409
0.7927	Intermediate Similarity	NPC29447
0.7922	Intermediate Similarity	NPC470525
0.7907	Intermediate Similarity	NPC263780
0.7907	Intermediate Similarity	NPC152897
0.7907	Intermediate Similarity	NPC66429
0.7901	Intermediate Similarity	NPC168188
0.7901	Intermediate Similarity	NPC477852
0.7901	Intermediate Similarity	NPC215893
0.7901	Intermediate Similarity	NPC167103
0.7901	Intermediate Similarity	NPC105803
0.7901	Intermediate Similarity	NPC470015
0.7895	Intermediate Similarity	NPC255168
0.7895	Intermediate Similarity	NPC18819
0.7895	Intermediate Similarity	NPC55527
0.7895	Intermediate Similarity	NPC46610
0.7882	Intermediate Similarity	NPC123854
0.7875	Intermediate Similarity	NPC14203
0.7875	Intermediate Similarity	NPC40228
0.7875	Intermediate Similarity	NPC229584
0.7875	Intermediate Similarity	NPC90055
0.7875	Intermediate Similarity	NPC55869
0.7875	Intermediate Similarity	NPC474955
0.7867	Intermediate Similarity	NPC72343
0.7857	Intermediate Similarity	NPC294480
0.7848	Intermediate Similarity	NPC192329
0.7848	Intermediate Similarity	NPC27817
0.7831	Intermediate Similarity	NPC6247
0.7831	Intermediate Similarity	NPC28252
0.7831	Intermediate Similarity	NPC55309
0.7831	Intermediate Similarity	NPC325594
0.7831	Intermediate Similarity	NPC473226
0.7831	Intermediate Similarity	NPC82979
0.7831	Intermediate Similarity	NPC324063
0.7831	Intermediate Similarity	NPC212843
0.7831	Intermediate Similarity	NPC262085
0.7831	Intermediate Similarity	NPC73038
0.7831	Intermediate Similarity	NPC155011
0.7821	Intermediate Similarity	NPC257666
0.7821	Intermediate Similarity	NPC266193
0.7816	Intermediate Similarity	NPC80365
0.7816	Intermediate Similarity	NPC469406
0.7808	Intermediate Similarity	NPC472875
0.7805	Intermediate Similarity	NPC472864
0.7805	Intermediate Similarity	NPC248758
0.7805	Intermediate Similarity	NPC194937
0.7805	Intermediate Similarity	NPC19849
0.7805	Intermediate Similarity	NPC476038
0.7792	Intermediate Similarity	NPC472327
0.7791	Intermediate Similarity	NPC45269
0.7791	Intermediate Similarity	NPC470036
0.7791	Intermediate Similarity	NPC174167
0.7765	Intermediate Similarity	NPC474686
0.7763	Intermediate Similarity	NPC109576
0.7763	Intermediate Similarity	NPC130016
0.7763	Intermediate Similarity	NPC180015
0.7763	Intermediate Similarity	NPC56747
0.7763	Intermediate Similarity	NPC177826
0.775	Intermediate Similarity	NPC2482
0.775	Intermediate Similarity	NPC476809
0.775	Intermediate Similarity	NPC267517
0.7738	Intermediate Similarity	NPC474684
0.7738	Intermediate Similarity	NPC181327
0.7738	Intermediate Similarity	NPC307426
0.7738	Intermediate Similarity	NPC130577
0.7738	Intermediate Similarity	NPC102683

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 NPC301065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1711
0.2-0.3	3882
0.3-0.4	2264
0.4-0.5	680
0.5-0.6	320
0.6-0.7	112
0.7-0.8	19
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
0.8	Intermediate Similarity	NPD5281	Approved
0.8	Intermediate Similarity	NPD5284	Approved
0.7976	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4694	Approved
0.7831	Intermediate Similarity	NPD5280	Approved
0.7619	Intermediate Similarity	NPD5279	Phase 3
0.7586	Intermediate Similarity	NPD6411	Approved
0.7561	Intermediate Similarity	NPD4221	Approved
0.7561	Intermediate Similarity	NPD3667	Approved
0.7561	Intermediate Similarity	NPD4223	Phase 3
0.7531	Intermediate Similarity	NPD4695	Discontinued
0.7471	Intermediate Similarity	NPD5692	Phase 3
0.7471	Intermediate Similarity	NPD5207	Approved
0.7412	Intermediate Similarity	NPD5690	Phase 2
0.7391	Intermediate Similarity	NPD6404	Discontinued
0.7386	Intermediate Similarity	NPD5694	Approved
0.7386	Intermediate Similarity	NPD7515	Phase 2
0.7386	Intermediate Similarity	NPD6050	Approved
0.7381	Intermediate Similarity	NPD4197	Approved
0.7381	Intermediate Similarity	NPD3133	Approved
0.7381	Intermediate Similarity	NPD3666	Approved
0.7381	Intermediate Similarity	NPD3665	Phase 1
0.7381	Intermediate Similarity	NPD4786	Approved
0.7356	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6101	Approved
0.7342	Intermediate Similarity	NPD8039	Approved
0.7333	Intermediate Similarity	NPD5695	Phase 3
0.7303	Intermediate Similarity	NPD6399	Phase 3
0.7294	Intermediate Similarity	NPD5329	Approved
0.7284	Intermediate Similarity	NPD3617	Approved
0.7273	Intermediate Similarity	NPD4096	Approved
0.7241	Intermediate Similarity	NPD4518	Approved
0.7229	Intermediate Similarity	NPD4692	Approved
0.7229	Intermediate Similarity	NPD4139	Approved
0.7222	Intermediate Similarity	NPD7748	Approved
0.7215	Intermediate Similarity	NPD4687	Approved
0.7215	Intermediate Similarity	NPD5733	Approved
0.7209	Intermediate Similarity	NPD7521	Approved
0.7209	Intermediate Similarity	NPD7334	Approved
0.7209	Intermediate Similarity	NPD6684	Approved
0.7209	Intermediate Similarity	NPD6098	Approved
0.7209	Intermediate Similarity	NPD7146	Approved
0.7209	Intermediate Similarity	NPD4138	Approved
0.7209	Intermediate Similarity	NPD4690	Approved
0.7209	Intermediate Similarity	NPD6409	Approved
0.7209	Intermediate Similarity	NPD4693	Phase 3
0.7209	Intermediate Similarity	NPD5205	Approved
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7209	Intermediate Similarity	NPD4689	Approved
0.7209	Intermediate Similarity	NPD4623	Approved
0.7209	Intermediate Similarity	NPD4688	Approved
0.7209	Intermediate Similarity	NPD5330	Approved
0.7209	Intermediate Similarity	NPD4519	Discontinued
0.7179	Intermediate Similarity	NPD5276	Approved
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3573	Approved
0.7111	Intermediate Similarity	NPD5779	Approved
0.7111	Intermediate Similarity	NPD5133	Approved
0.7111	Intermediate Similarity	NPD5778	Approved
0.7065	Intermediate Similarity	NPD7614	Phase 1
0.7045	Intermediate Similarity	NPD6672	Approved
0.7045	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6903	Approved
0.7045	Intermediate Similarity	NPD5737	Approved
0.7045	Intermediate Similarity	NPD5208	Approved
0.7011	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4058	Approved
0.6989	Remote Similarity	NPD6084	Phase 2
0.6989	Remote Similarity	NPD7902	Approved
0.6989	Remote Similarity	NPD6083	Phase 2
0.6977	Remote Similarity	NPD3668	Phase 3
0.6974	Remote Similarity	NPD7331	Phase 2
0.6966	Remote Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD6080	Approved
0.6966	Remote Similarity	NPD6904	Approved
0.6966	Remote Similarity	NPD5328	Approved
0.6966	Remote Similarity	NPD6673	Approved
0.6957	Remote Similarity	NPD3172	Approved
0.6957	Remote Similarity	NPD5654	Approved
0.6923	Remote Similarity	NPD4137	Phase 3
0.6915	Remote Similarity	NPD5696	Approved
0.6897	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4192	Approved
0.6892	Remote Similarity	NPD4193	Approved
0.6892	Remote Similarity	NPD4191	Approved
0.6892	Remote Similarity	NPD4194	Approved
0.6857	Remote Similarity	NPD3194	Approved
0.6857	Remote Similarity	NPD3196	Approved
0.6857	Remote Similarity	NPD4266	Approved
0.6857	Remote Similarity	NPD3195	Phase 2
0.6842	Remote Similarity	NPD7341	Phase 2
0.6835	Remote Similarity	NPD4747	Approved
0.6835	Remote Similarity	NPD4691	Approved
0.6824	Remote Similarity	NPD857	Phase 3
0.6813	Remote Similarity	NPD6079	Approved
0.6813	Remote Similarity	NPD5693	Phase 1
0.6809	Remote Similarity	NPD5959	Approved
0.6795	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4195	Approved
0.6753	Remote Similarity	NPD4224	Phase 2
0.675	Remote Similarity	NPD4243	Approved
0.6739	Remote Similarity	NPD4202	Approved
0.6707	Remote Similarity	NPD8264	Approved
0.6706	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5210	Approved
0.6596	Remote Similarity	NPD4629	Approved
0.6596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4785	Approved
0.6585	Remote Similarity	NPD4784	Approved
0.6585	Remote Similarity	NPD6926	Approved
0.6585	Remote Similarity	NPD6924	Approved
0.6559	Remote Similarity	NPD1088	Approved
0.6526	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5221	Approved
0.6526	Remote Similarity	NPD5222	Approved
0.6526	Remote Similarity	NPD4697	Phase 3
0.6526	Remote Similarity	NPD7732	Phase 3
0.6517	Remote Similarity	NPD1694	Approved
0.6506	Remote Similarity	NPD4190	Phase 3
0.6506	Remote Similarity	NPD6942	Approved
0.6506	Remote Similarity	NPD7339	Approved
0.6506	Remote Similarity	NPD5275	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6489	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD287	Approved
0.6477	Remote Similarity	NPD4788	Approved
0.6477	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4755	Approved
0.6458	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD5701	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6429	Remote Similarity	NPD28	Approved
0.6429	Remote Similarity	NPD6933	Approved
0.6429	Remote Similarity	NPD29	Approved
0.6395	Remote Similarity	NPD7645	Phase 2
0.6392	Remote Similarity	NPD7638	Approved
0.6377	Remote Similarity	NPD3173	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6353	Remote Similarity	NPD4756	Discovery
0.6344	Remote Similarity	NPD1086	Approved
0.6344	Remote Similarity	NPD1090	Approved
0.6344	Remote Similarity	NPD1089	Approved
0.6341	Remote Similarity	NPD6081	Approved
0.6333	Remote Similarity	NPD1696	Phase 3
0.6327	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD7639	Approved
0.6327	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD5286	Approved
0.6327	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD5285	Approved
0.6322	Remote Similarity	NPD5368	Approved
0.6311	Remote Similarity	NPD6373	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6296	Remote Similarity	NPD6922	Approved
0.6296	Remote Similarity	NPD6923	Approved
0.6292	Remote Similarity	NPD5362	Discontinued
0.6282	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7637	Suspended
0.6263	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6883	Approved
0.6237	Remote Similarity	NPD5346	Phase 2
0.6237	Remote Similarity	NPD800	Approved
0.6237	Remote Similarity	NPD5347	Phase 2
0.6232	Remote Similarity	NPD622	Approved
0.622	Remote Similarity	NPD7143	Approved
0.622	Remote Similarity	NPD7144	Approved
0.6207	Remote Similarity	NPD6929	Approved
0.6203	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5091	Approved
0.62	Remote Similarity	NPD5225	Approved
0.62	Remote Similarity	NPD5226	Approved
0.62	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD4633	Approved
0.62	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6649	Approved
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD8130	Phase 1

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