NPASS Compound

Structure

NPC259576 OpenBabel07101718202D 39 42 0 0 1 0 0 0 0 0999 V2000 6.0622 -3.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 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 6.9282 -2.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 6.9282 -5.0000 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 7.7942 -4.5000 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 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 6.0622 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -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 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 5.1962 -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 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 14 1 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 8 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 21 2 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 22 11 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 0 0 0 0 23 32 2 0 0 0 0 23 37 1 0 0 0 0 24 15 1 1 0 0 0 24 25 1 0 0 0 0 24 38 1 0 0 0 0 25 27 1 1 0 0 0 25 39 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.11
Volume:	512.531
LogP:	1.906
LogD:	2.017
LogS:	-4.821
# Rotatable Bonds:	9
TPSA:	200.28
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	3.859
Fsp3:	0.148
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.316
MDCK Permeability:	8.129444722726475e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.308
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	95.50643157958984%
Volume Distribution (VD):	0.348
Pgp-substrate:	1.9679248332977295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	7.719
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.447
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.89
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.632
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.814
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC259576

Natural Product ID:	NPC259576
*Common Name:**	Clinopodic Acid C
IUPAC Name:	(2S,3S)-6-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-3-carboxylic acid
Synonyms:	Clinopodic Acid C
Standard InCHIKey:	KPKHMGUZUPELJC-RXYMDKBQSA-N
Standard InCHI:	InChI=1S/C27H22O12/c28-16-5-1-14(9-18(16)30)11-22(26(33)34)37-23(32)8-3-13-2-7-20-21(10-13)39-25(27(35)36)24(38-20)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-31H,11H2,(H,33,34)(H,35,36)/p-2/b8-3+/t22-,24+,25+/m1/s1
SMILES:	c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c1ccc2c(c1)O[C@@H]([C@H](c1ccc(c(c1)O)[O-])O2)C(=O)O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080779
PubChem CID:	44254596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO13475.1	Clinopodium chinense	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19711986]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT40	Individual Protein	72 kDa type IV collagenase	Rattus norvegicus	IC50	=	3260.0	nM	PMID[542329]

☑ 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 NPC259576 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	363
0.1-0.2	1446
0.2-0.3	3801
0.3-0.4	8510
0.4-0.5	9659
0.5-0.6	3833
0.6-0.7	6411
0.7-0.8	7467
0.8-0.85	1066
0.85-0.9	117
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221091
0.993	High Similarity	NPC300329
0.9577	High Similarity	NPC160378
0.9161	High Similarity	NPC288452
0.9161	High Similarity	NPC289690
0.9116	High Similarity	NPC283081
0.9116	High Similarity	NPC221383
0.9116	High Similarity	NPC299090
0.9116	High Similarity	NPC143892
0.9032	High Similarity	NPC144557
0.9026	High Similarity	NPC44507
0.902	High Similarity	NPC40920
0.902	High Similarity	NPC223335
0.898	High Similarity	NPC53884
0.898	High Similarity	NPC258671
0.8974	High Similarity	NPC173729
0.8974	High Similarity	NPC134047
0.8974	High Similarity	NPC223006
0.8974	High Similarity	NPC272750
0.8961	High Similarity	NPC469654
0.8954	High Similarity	NPC473275
0.8954	High Similarity	NPC470896
0.8951	High Similarity	NPC471664
0.8951	High Similarity	NPC471665
0.8947	High Similarity	NPC469888
0.894	High Similarity	NPC95498
0.894	High Similarity	NPC246566
0.8912	High Similarity	NPC304956
0.8903	High Similarity	NPC301089
0.8889	High Similarity	NPC126206
0.8889	High Similarity	NPC131532
0.8882	High Similarity	NPC44730
0.8882	High Similarity	NPC474656
0.8868	High Similarity	NPC41494
0.8868	High Similarity	NPC186100
0.8868	High Similarity	NPC216403
0.8867	High Similarity	NPC98809
0.8867	High Similarity	NPC476394
0.8851	High Similarity	NPC473909
0.8851	High Similarity	NPC143120
0.8851	High Similarity	NPC274960
0.8824	High Similarity	NPC477299
0.8811	High Similarity	NPC106406
0.8803	High Similarity	NPC18074
0.8803	High Similarity	NPC25581
0.8803	High Similarity	NPC5419
0.8803	High Similarity	NPC61
0.88	High Similarity	NPC1580
0.88	High Similarity	NPC192568
0.88	High Similarity	NPC472969
0.88	High Similarity	NPC471076
0.8792	High Similarity	NPC40222
0.8792	High Similarity	NPC268515
0.8782	High Similarity	NPC53889
0.8774	High Similarity	NPC160512
0.8774	High Similarity	NPC38779
0.8774	High Similarity	NPC156818
0.8774	High Similarity	NPC133984
0.8774	High Similarity	NPC68324
0.8774	High Similarity	NPC289322
0.8774	High Similarity	NPC114179
0.8767	High Similarity	NPC179505
0.8767	High Similarity	NPC156709
0.8758	High Similarity	NPC476370
0.875	High Similarity	NPC243891
0.8741	High Similarity	NPC155209
0.8741	High Similarity	NPC168799
0.8732	High Similarity	NPC198388
0.8726	High Similarity	NPC112418
0.8718	High Similarity	NPC87317
0.871	High Similarity	NPC250436
0.871	High Similarity	NPC300845
0.871	High Similarity	NPC88803
0.871	High Similarity	NPC291948
0.871	High Similarity	NPC104983
0.8707	High Similarity	NPC38473
0.8704	High Similarity	NPC476374
0.8693	High Similarity	NPC267091
0.8693	High Similarity	NPC476434
0.8693	High Similarity	NPC163883
0.8693	High Similarity	NPC93498
0.8688	High Similarity	NPC128403
0.8681	High Similarity	NPC135127
0.8671	High Similarity	NPC471745
0.8667	High Similarity	NPC98356
0.8662	High Similarity	NPC476373
0.8662	High Similarity	NPC471744
0.8662	High Similarity	NPC24164
0.8659	High Similarity	NPC139571
0.8659	High Similarity	NPC217520
0.865	High Similarity	NPC34267
0.865	High Similarity	NPC214621
0.865	High Similarity	NPC81042
0.865	High Similarity	NPC223426
0.8649	High Similarity	NPC67467
0.8636	High Similarity	NPC19380
0.8636	High Similarity	NPC146277
0.8634	High Similarity	NPC280493
0.863	High Similarity	NPC279676
0.863	High Similarity	NPC67349
0.8621	High Similarity	NPC214729
0.8618	High Similarity	NPC111785
0.8618	High Similarity	NPC475250
0.8616	High Similarity	NPC227297
0.8609	High Similarity	NPC229264
0.8608	High Similarity	NPC71780
0.8608	High Similarity	NPC216916
0.86	High Similarity	NPC477333
0.8598	High Similarity	NPC61904
0.8598	High Similarity	NPC144097
0.8592	High Similarity	NPC241354
0.8591	High Similarity	NPC319628
0.8591	High Similarity	NPC220664
0.8591	High Similarity	NPC284948
0.8591	High Similarity	NPC303090
0.8591	High Similarity	NPC37331
0.8591	High Similarity	NPC478239
0.859	High Similarity	NPC471405
0.859	High Similarity	NPC318432
0.8581	High Similarity	NPC194095
0.8581	High Similarity	NPC327032
0.8581	High Similarity	NPC191046
0.8581	High Similarity	NPC186406
0.858	High Similarity	NPC149011
0.858	High Similarity	NPC204937
0.858	High Similarity	NPC476365
0.8571	High Similarity	NPC163598
0.8571	High Similarity	NPC120774
0.8571	High Similarity	NPC75695
0.8571	High Similarity	NPC284409
0.8571	High Similarity	NPC469521
0.8571	High Similarity	NPC264875
0.8562	High Similarity	NPC36
0.8562	High Similarity	NPC142614
0.8562	High Similarity	NPC36916
0.8562	High Similarity	NPC125039
0.8562	High Similarity	NPC7688
0.8562	High Similarity	NPC32197
0.8562	High Similarity	NPC58223
0.8562	High Similarity	NPC7154
0.8562	High Similarity	NPC72787
0.8553	High Similarity	NPC476372
0.8553	High Similarity	NPC187398
0.8553	High Similarity	NPC473138
0.8553	High Similarity	NPC476371
0.8553	High Similarity	NPC28776
0.8553	High Similarity	NPC285108
0.8553	High Similarity	NPC476348
0.8553	High Similarity	NPC116229
0.8553	High Similarity	NPC33298
0.8545	High Similarity	NPC477895
0.8545	High Similarity	NPC37668
0.8545	High Similarity	NPC113836
0.8545	High Similarity	NPC253521
0.8545	High Similarity	NPC35167
0.8544	High Similarity	NPC289346
0.8537	High Similarity	NPC473630
0.8535	High Similarity	NPC471515
0.8535	High Similarity	NPC471479
0.8533	High Similarity	NPC470130
0.8533	High Similarity	NPC183824
0.8533	High Similarity	NPC473090
0.8533	High Similarity	NPC232228
0.8528	High Similarity	NPC153755
0.8526	High Similarity	NPC10205
0.8526	High Similarity	NPC145425
0.8523	High Similarity	NPC206095
0.8523	High Similarity	NPC224389
0.8523	High Similarity	NPC35702
0.8523	High Similarity	NPC477335
0.8523	High Similarity	NPC297517
0.8523	High Similarity	NPC140502
0.8523	High Similarity	NPC471027
0.8523	High Similarity	NPC13818
0.8523	High Similarity	NPC157816
0.8519	High Similarity	NPC476279
0.8516	High Similarity	NPC157898
0.8503	High Similarity	NPC470718
0.8503	High Similarity	NPC36138
0.85	High Similarity	NPC45943
0.85	High Similarity	NPC121290
0.8497	Intermediate Similarity	NPC30688
0.8497	Intermediate Similarity	NPC478242
0.8497	Intermediate Similarity	NPC176903
0.8491	Intermediate Similarity	NPC469889
0.8491	Intermediate Similarity	NPC113163
0.8491	Intermediate Similarity	NPC305987
0.8491	Intermediate Similarity	NPC165970
0.8491	Intermediate Similarity	NPC66618
0.8491	Intermediate Similarity	NPC84324
0.8491	Intermediate Similarity	NPC288131
0.8491	Intermediate Similarity	NPC158188
0.8487	Intermediate Similarity	NPC322660
0.8487	Intermediate Similarity	NPC476347
0.8485	Intermediate Similarity	NPC296018
0.8485	Intermediate Similarity	NPC154741
0.8483	Intermediate Similarity	NPC475468
0.8481	Intermediate Similarity	NPC476410
0.8481	Intermediate Similarity	NPC284127
0.8481	Intermediate Similarity	NPC172202

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 NPC259576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	855
0.2-0.3	1725
0.3-0.4	2562
0.4-0.5	1873
0.5-0.6	1050
0.6-0.7	619
0.7-0.8	138
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD4868	Clinical (unspecified phase)
0.8591	High Similarity	NPD6190	Approved
0.8562	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD6166	Phase 2
0.8562	High Similarity	NPD6168	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD3817	Phase 2
0.8345	Intermediate Similarity	NPD6233	Phase 2
0.8303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1934	Approved
0.8239	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD6797	Phase 2
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8176	Intermediate Similarity	NPD5402	Approved
0.8151	Intermediate Similarity	NPD6798	Discontinued
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8113	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8079	Intermediate Similarity	NPD7266	Discontinued
0.8077	Intermediate Similarity	NPD5403	Approved
0.8072	Intermediate Similarity	NPD7054	Approved
0.8024	Intermediate Similarity	NPD7074	Phase 3
0.8024	Intermediate Similarity	NPD7472	Approved
0.8013	Intermediate Similarity	NPD1512	Approved
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2801	Approved
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7953	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5401	Approved
0.7911	Intermediate Similarity	NPD1653	Approved
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.7885	Intermediate Similarity	NPD6799	Approved
0.7885	Intermediate Similarity	NPD1511	Approved
0.7853	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD4380	Phase 2
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.78	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1613	Approved
0.7798	Intermediate Similarity	NPD3751	Discontinued
0.7793	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7764	Intermediate Similarity	NPD7411	Suspended
0.7748	Intermediate Similarity	NPD6355	Discontinued
0.7733	Intermediate Similarity	NPD4062	Phase 3
0.7719	Intermediate Similarity	NPD7685	Pre-registration
0.7718	Intermediate Similarity	NPD7095	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD8455	Phase 2
0.7665	Intermediate Similarity	NPD3787	Discontinued
0.7651	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7473	Discontinued
0.7632	Intermediate Similarity	NPD447	Suspended
0.7632	Intermediate Similarity	NPD4340	Discontinued
0.763	Intermediate Similarity	NPD8313	Approved
0.763	Intermediate Similarity	NPD8312	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7593	Intermediate Similarity	NPD6599	Discontinued
0.7584	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7576	Intermediate Similarity	NPD7768	Phase 2
0.7576	Intermediate Similarity	NPD4965	Approved
0.7566	Intermediate Similarity	NPD4060	Phase 1
0.7564	Intermediate Similarity	NPD1549	Phase 2
0.7561	Intermediate Similarity	NPD7819	Suspended
0.7548	Intermediate Similarity	NPD2935	Discontinued
0.7545	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7038	Approved
0.7514	Intermediate Similarity	NPD7039	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4110	Phase 3
0.7468	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD8166	Discontinued
0.7436	Intermediate Similarity	NPD1551	Phase 2
0.7434	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6959	Discontinued
0.7391	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD919	Approved
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7351	Intermediate Similarity	NPD9494	Approved
0.7342	Intermediate Similarity	NPD4534	Discontinued
0.7342	Intermediate Similarity	NPD5958	Discontinued
0.7333	Intermediate Similarity	NPD1203	Approved
0.7321	Intermediate Similarity	NPD3749	Approved
0.732	Intermediate Similarity	NPD3764	Approved
0.7317	Intermediate Similarity	NPD3226	Approved
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7308	Intermediate Similarity	NPD7097	Phase 1
0.7303	Intermediate Similarity	NPD6832	Phase 2
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7297	Intermediate Similarity	NPD1535	Discovery
0.7284	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3146	Approved
0.7267	Intermediate Similarity	NPD7440	Discontinued
0.7267	Intermediate Similarity	NPD3225	Approved
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD1894	Discontinued
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD1481	Phase 2
0.7239	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD2861	Phase 2
0.7229	Intermediate Similarity	NPD6385	Approved
0.7229	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2796	Approved
0.7212	Intermediate Similarity	NPD3455	Phase 2
0.7209	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7549	Discontinued
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD6653	Approved
0.7133	Intermediate Similarity	NPD228	Approved
0.7125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6971	Discontinued
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.7099	Intermediate Similarity	NPD3887	Approved
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD3268	Approved
0.7093	Intermediate Similarity	NPD1247	Approved
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.7081	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD5647	Approved
0.7048	Intermediate Similarity	NPD3687	Approved
0.7048	Intermediate Similarity	NPD3686	Approved
0.7047	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7027	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD1558	Phase 1
0.7006	Intermediate Similarity	NPD943	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6983	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5585	Approved
0.6971	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3536	Discontinued
0.697	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5535	Approved
0.6964	Remote Similarity	NPD4972	Discontinued
0.6962	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5124	Phase 1
0.6954	Remote Similarity	NPD1610	Phase 2
0.6954	Remote Similarity	NPD1091	Approved
0.6954	Remote Similarity	NPD422	Phase 1
0.6947	Remote Similarity	NPD7680	Approved
0.6937	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD1778	Approved
0.6933	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7003	Approved
0.6931	Remote Similarity	NPD3450	Approved
0.6931	Remote Similarity	NPD3452	Approved
0.6931	Remote Similarity	NPD2494	Approved
0.6931	Remote Similarity	NPD2493	Approved
0.6928	Remote Similarity	NPD5049	Phase 3
0.6918	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD5283	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