NPASS Compound

Structure

NPC173729 OpenBabel07101719252D 41 44 0 0 1 0 0 0 0 0999 V2000 11.1354 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5374 -2.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5374 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4034 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0933 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4034 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5933 -2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -1.3309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2694 -2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5933 -4.3776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 -2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7614 -2.5032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -1.3443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2694 -0.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5933 -2.6456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.8309 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 38 1 0 0 0 0 2 39 1 0 0 0 0 3 7 2 0 0 0 0 3 14 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 15 24 2 0 0 0 0 17 20 2 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 31 1 0 0 0 0 19 27 2 0 0 0 0 19 32 1 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 22 12 1 6 0 0 0 22 28 1 0 0 0 0 22 40 1 0 0 0 0 23 33 2 0 0 0 0 23 40 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 6 0 0 0 26 16 1 1 0 0 0 26 41 1 0 0 0 0 27 41 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.14
Volume:	547.123
LogP:	2.418
LogD:	6.935
LogS:	-4.067
# Rotatable Bonds:	11
TPSA:	189.28
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	3.945
Fsp3:	0.207
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.108
MDCK Permeability:	9.971504368877504e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.08592987060547%
Volume Distribution (VD):	0.272
Pgp-substrate:	4.682305335998535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.789
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	3.929
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.355
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.453
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC173729

Natural Product ID:	NPC173729
*Common Name:**	Clinopodic Acid H
IUPAC Name:	(2S,3S)-4-[(E)-3-[(1R)-1-carboxy-2-(4-hydroxy-3-methoxyphenyl)ethoxy]-3-oxoprop-1-enyl]-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid
Synonyms:	Clinopodic Acid H
Standard InCHIKey:	QQPFHBFQFCFWRM-ZBBBDWFHSA-N
Standard InCHI:	InChI=1S/C29H26O12/c1-38-20-11-14(3-7-17(20)30)12-22(28(34)35)40-23(33)10-6-15-4-9-19(32)27-24(15)25(29(36)37)26(41-27)16-5-8-18(31)21(13-16)39-2/h3-11,13,22,25-26,30-32H,12H2,1-2H3,(H,34,35)(H,36,37)/b10-6+/t22-,25+,26-/m1/s1
SMILES:	COc1cc(ccc1O)C[C@H](C(=O)O)OC(=O)/C=C/c1ccc(c2c1[C@@H]([C@@H](c1ccc(c(c1)OC)O)O2)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079357
PubChem CID:	44254598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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	>	100000.0	nM	PMID[525663]

☑ 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 NPC173729 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	376
0.1-0.2	1405
0.2-0.3	3170
0.3-0.4	7421
0.4-0.5	10195
0.5-0.6	4528
0.6-0.7	5297
0.7-0.8	7774
0.8-0.85	2306
0.85-0.9	208
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC272750
1.0	High Similarity	NPC223006
1.0	High Similarity	NPC134047
0.9935	High Similarity	NPC144557
0.9623	High Similarity	NPC186100
0.9623	High Similarity	NPC216403
0.9623	High Similarity	NPC41494
0.9125	High Similarity	NPC469889
0.9103	High Similarity	NPC267091
0.9062	High Similarity	NPC472962
0.9062	High Similarity	NPC472961
0.9038	High Similarity	NPC243891
0.9038	High Similarity	NPC300329
0.9012	High Similarity	NPC45943
0.8974	High Similarity	NPC259576
0.8974	High Similarity	NPC221091
0.8935	High Similarity	NPC475996
0.8889	High Similarity	NPC216916
0.8861	High Similarity	NPC476434
0.8855	High Similarity	NPC91043
0.8831	High Similarity	NPC160378
0.8827	High Similarity	NPC301089
0.8827	High Similarity	NPC53889
0.8812	High Similarity	NPC80489
0.8805	High Similarity	NPC44730
0.8805	High Similarity	NPC295646
0.8802	High Similarity	NPC476370
0.8802	High Similarity	NPC247964
0.8788	High Similarity	NPC477517
0.8782	High Similarity	NPC299090
0.8782	High Similarity	NPC283081
0.8782	High Similarity	NPC221383
0.8782	High Similarity	NPC143892
0.8773	High Similarity	NPC112418
0.8765	High Similarity	NPC87317
0.875	High Similarity	NPC316539
0.875	High Similarity	NPC476374
0.8743	High Similarity	NPC279209
0.8743	High Similarity	NPC180768
0.8743	High Similarity	NPC102277
0.8735	High Similarity	NPC215802
0.8735	High Similarity	NPC167231
0.8728	High Similarity	NPC475360
0.8726	High Similarity	NPC472969
0.872	High Similarity	NPC164937
0.872	High Similarity	NPC471745
0.872	High Similarity	NPC144843
0.8713	High Similarity	NPC170203
0.8712	High Similarity	NPC471744
0.8704	High Similarity	NPC289322
0.8704	High Similarity	NPC38779
0.8704	High Similarity	NPC114179
0.8704	High Similarity	NPC160512
0.8704	High Similarity	NPC156818
0.8704	High Similarity	NPC143328
0.8704	High Similarity	NPC68324
0.8701	High Similarity	NPC67467
0.8696	High Similarity	NPC180901
0.8696	High Similarity	NPC300757
0.8688	High Similarity	NPC131121
0.8683	High Similarity	NPC280493
0.8678	High Similarity	NPC205721
0.8675	High Similarity	NPC472452
0.8675	High Similarity	NPC43065
0.8671	High Similarity	NPC98809
0.8671	High Similarity	NPC476394
0.8667	High Similarity	NPC89131
0.8655	High Similarity	NPC244903
0.8654	High Similarity	NPC53884
0.8654	High Similarity	NPC258671
0.8654	High Similarity	NPC223185
0.8647	High Similarity	NPC154741
0.8647	High Similarity	NPC296018
0.8642	High Similarity	NPC291948
0.8642	High Similarity	NPC88803
0.8642	High Similarity	NPC227062
0.8642	High Similarity	NPC150227
0.8642	High Similarity	NPC104983
0.8642	High Similarity	NPC470896
0.8642	High Similarity	NPC54928
0.8642	High Similarity	NPC300845
0.8642	High Similarity	NPC250436
0.8642	High Similarity	NPC473275
0.8636	High Similarity	NPC38473
0.8634	High Similarity	NPC469888
0.8634	High Similarity	NPC477299
0.8625	High Similarity	NPC246566
0.8625	High Similarity	NPC95498
0.8623	High Similarity	NPC298847
0.8623	High Similarity	NPC150131
0.8623	High Similarity	NPC311912
0.8608	High Similarity	NPC192568
0.8608	High Similarity	NPC471076
0.8608	High Similarity	NPC236166
0.8606	High Similarity	NPC22324
0.8606	High Similarity	NPC42797
0.8606	High Similarity	NPC272722
0.8606	High Similarity	NPC473445
0.8598	High Similarity	NPC200594
0.8598	High Similarity	NPC47623
0.8598	High Similarity	NPC24164
0.8598	High Similarity	NPC24627
0.8598	High Similarity	NPC44507
0.8598	High Similarity	NPC155101
0.8596	High Similarity	NPC98546
0.8596	High Similarity	NPC476773
0.8596	High Similarity	NPC297807
0.859	High Similarity	NPC304956
0.8589	High Similarity	NPC223335
0.8589	High Similarity	NPC299520
0.8589	High Similarity	NPC129684
0.8589	High Similarity	NPC40920
0.8589	High Similarity	NPC77679
0.8589	High Similarity	NPC471479
0.8589	High Similarity	NPC190020
0.8589	High Similarity	NPC84935
0.8589	High Similarity	NPC471515
0.8588	High Similarity	NPC287243
0.8581	High Similarity	NPC253722
0.8581	High Similarity	NPC31751
0.8581	High Similarity	NPC253481
0.858	High Similarity	NPC79998
0.858	High Similarity	NPC199926
0.858	High Similarity	NPC268008
0.858	High Similarity	NPC469506
0.8571	High Similarity	NPC65591
0.8571	High Similarity	NPC473236
0.8571	High Similarity	NPC178574
0.8571	High Similarity	NPC289690
0.8571	High Similarity	NPC88557
0.8571	High Similarity	NPC115203
0.8571	High Similarity	NPC288452
0.8554	High Similarity	NPC291977
0.8554	High Similarity	NPC475985
0.8545	High Similarity	NPC92589
0.8544	High Similarity	NPC85734
0.8544	High Similarity	NPC229264
0.8544	High Similarity	NPC32058
0.8538	High Similarity	NPC473713
0.8537	High Similarity	NPC471750
0.8537	High Similarity	NPC55738
0.8537	High Similarity	NPC469654
0.8537	High Similarity	NPC195832
0.8535	High Similarity	NPC163898
0.8529	High Similarity	NPC476640
0.8529	High Similarity	NPC82217
0.8529	High Similarity	NPC216842
0.8529	High Similarity	NPC474568
0.8528	High Similarity	NPC478055
0.8528	High Similarity	NPC163635
0.8528	High Similarity	NPC165483
0.8528	High Similarity	NPC471500
0.8528	High Similarity	NPC265511
0.8528	High Similarity	NPC318432
0.8523	High Similarity	NPC295436
0.8523	High Similarity	NPC201814
0.8521	High Similarity	NPC476365
0.8521	High Similarity	NPC72249
0.8521	High Similarity	NPC477883
0.8519	High Similarity	NPC281703
0.8519	High Similarity	NPC25127
0.8519	High Similarity	NPC287504
0.8519	High Similarity	NPC125487
0.8516	High Similarity	NPC100675
0.8514	High Similarity	NPC269625
0.8512	High Similarity	NPC186392
0.8512	High Similarity	NPC469521
0.8512	High Similarity	NPC283041
0.8509	High Similarity	NPC163883
0.8509	High Similarity	NPC93498
0.8509	High Similarity	NPC270268
0.8509	High Similarity	NPC75695
0.8503	High Similarity	NPC36
0.8503	High Similarity	NPC142614
0.8503	High Similarity	NPC36320
0.8503	High Similarity	NPC58223
0.8503	High Similarity	NPC471788
0.8503	High Similarity	NPC326520
0.8503	High Similarity	NPC125039
0.8503	High Similarity	NPC72787
0.8503	High Similarity	NPC472277
0.8503	High Similarity	NPC191930
0.8503	High Similarity	NPC45449
0.8503	High Similarity	NPC36916
0.8503	High Similarity	NPC7688
0.8503	High Similarity	NPC7154
0.8497	Intermediate Similarity	NPC47883
0.8494	Intermediate Similarity	NPC249070
0.8494	Intermediate Similarity	NPC476372
0.8494	Intermediate Similarity	NPC472964
0.8494	Intermediate Similarity	NPC476371
0.8491	Intermediate Similarity	NPC98009
0.8491	Intermediate Similarity	NPC1580
0.8488	Intermediate Similarity	NPC35167
0.8488	Intermediate Similarity	NPC139571
0.8488	Intermediate Similarity	NPC217520
0.8488	Intermediate Similarity	NPC47191
0.8485	Intermediate Similarity	NPC292415
0.8485	Intermediate Similarity	NPC36217
0.8485	Intermediate Similarity	NPC300680

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 NPC173729 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	881
0.2-0.3	1683
0.3-0.4	2526
0.4-0.5	1903
0.5-0.6	1060
0.6-0.7	572
0.7-0.8	177
0.8-0.85	27
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD3882	Suspended
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8554	High Similarity	NPD7184	Clinical (unspecified phase)
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8439	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD3818	Discontinued
0.8383	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD1934	Approved
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD7199	Phase 2
0.8313	Intermediate Similarity	NPD6234	Discontinued
0.8291	Intermediate Similarity	NPD6190	Approved
0.8266	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8246	Intermediate Similarity	NPD5844	Phase 1
0.8187	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD37	Approved
0.809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD4965	Approved
0.8084	Intermediate Similarity	NPD4967	Phase 2
0.8072	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5494	Approved
0.8046	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD6798	Discontinued
0.7977	Intermediate Similarity	NPD7228	Approved
0.7975	Intermediate Similarity	NPD1512	Approved
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7949	Intermediate Similarity	NPD6355	Discontinued
0.7931	Intermediate Similarity	NPD7054	Approved
0.7917	Intermediate Similarity	NPD5402	Approved
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7888	Intermediate Similarity	NPD4628	Phase 3
0.7886	Intermediate Similarity	NPD7472	Approved
0.7885	Intermediate Similarity	NPD4060	Phase 1
0.7877	Intermediate Similarity	NPD8434	Phase 2
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.7853	Intermediate Similarity	NPD1511	Approved
0.7831	Intermediate Similarity	NPD3226	Approved
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3749	Approved
0.7821	Intermediate Similarity	NPD6233	Phase 2
0.7818	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8313	Approved
0.7809	Intermediate Similarity	NPD8312	Approved
0.7805	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7685	Pre-registration
0.7791	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7738	Intermediate Similarity	NPD7411	Suspended
0.7719	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5403	Approved
0.7706	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7679	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7229	Phase 3
0.7643	Intermediate Similarity	NPD3764	Approved
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD5401	Approved
0.7586	Intermediate Similarity	NPD1247	Approved
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7578	Intermediate Similarity	NPD7033	Discontinued
0.7561	Intermediate Similarity	NPD3750	Approved
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7557	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1549	Phase 2
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD5763	Approved
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5762	Approved
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD7095	Approved
0.7468	Intermediate Similarity	NPD1608	Approved
0.7456	Intermediate Similarity	NPD1653	Approved
0.7455	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4110	Phase 3
0.7442	Intermediate Similarity	NPD8455	Phase 2
0.744	Intermediate Similarity	NPD6273	Approved
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2796	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7382	Intermediate Similarity	NPD2493	Approved
0.7382	Intermediate Similarity	NPD2494	Approved
0.7378	Intermediate Similarity	NPD7266	Discontinued
0.7366	Intermediate Similarity	NPD2488	Approved
0.7366	Intermediate Similarity	NPD2490	Approved
0.7362	Intermediate Similarity	NPD1510	Phase 2
0.7358	Intermediate Similarity	NPD4582	Approved
0.7358	Intermediate Similarity	NPD4583	Approved
0.7358	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD8166	Discontinued
0.7342	Intermediate Similarity	NPD9494	Approved
0.7325	Intermediate Similarity	NPD2797	Approved
0.7312	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4002	Approved
0.7306	Intermediate Similarity	NPD4004	Approved
0.7305	Intermediate Similarity	NPD2309	Approved
0.7296	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3450	Approved
0.7292	Intermediate Similarity	NPD3452	Approved
0.7284	Intermediate Similarity	NPD1933	Approved
0.7283	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4062	Phase 3
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3748	Approved
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7003	Approved
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6781	Approved
0.724	Intermediate Similarity	NPD6777	Approved
0.724	Intermediate Similarity	NPD6782	Approved
0.724	Intermediate Similarity	NPD6780	Approved
0.724	Intermediate Similarity	NPD6776	Approved
0.724	Intermediate Similarity	NPD6778	Approved
0.724	Intermediate Similarity	NPD6779	Approved
0.7233	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5958	Discontinued
0.7225	Intermediate Similarity	NPD6385	Approved
0.7225	Intermediate Similarity	NPD6386	Approved
0.7222	Intermediate Similarity	NPD1240	Approved
0.7222	Intermediate Similarity	NPD943	Approved
0.7216	Intermediate Similarity	NPD7680	Approved
0.7213	Intermediate Similarity	NPD7039	Approved
0.7213	Intermediate Similarity	NPD7038	Approved
0.7212	Intermediate Similarity	NPD1551	Phase 2
0.7212	Intermediate Similarity	NPD2438	Suspended
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7205	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7193	Intermediate Similarity	NPD920	Approved
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7188	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6674	Discontinued
0.7182	Intermediate Similarity	NPD7177	Discontinued
0.7176	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3146	Approved
0.7175	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2975	Approved
0.7173	Intermediate Similarity	NPD2973	Approved
0.7173	Intermediate Similarity	NPD2974	Approved
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6002	Phase 3
0.7169	Intermediate Similarity	NPD6005	Phase 3
0.7169	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1471	Phase 3
0.7169	Intermediate Similarity	NPD6004	Phase 3
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.715	Intermediate Similarity	NPD4580	Approved
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7134	Intermediate Similarity	NPD1607	Approved
0.7126	Intermediate Similarity	NPD2897	Discontinued
0.7126	Intermediate Similarity	NPD4534	Discontinued
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.7117	Intermediate Similarity	NPD3620	Phase 2

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