NPASS Compound

Structure

CID19311 OpenBabel06191715342D 23 24 0 0 1 0 0 0 0 0999 V2000 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 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 3.4641 0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 1 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.27
Volume:	361.097
LogP:	4.715
LogD:	3.847
LogS:	-4.384
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	4.068
Fsp3:	0.95
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:	-4.936
MDCK Permeability:	1.9709683328983374e-05
Pgp-inhibitor:	0.522
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.765
30% Bioavailability (F30%):	0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	92.94769287109375%
Volume Distribution (VD):	0.409
Pgp-substrate:	7.180594444274902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	6.169
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.69
Carcinogencity:	0.145
Eye Corrosion:	0.772
Eye Irritation:	0.628
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC19311

Natural Product ID:	NPC19311
*Common Name:**	Labdanic Acid
IUPAC Name:	(3S)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
Synonyms:	Labdanic Acid
Standard InCHIKey:	KHCCSRVJJDOANA-RQOBALISSA-N
Standard InCHI:	InChI=1S/C20H36O3/c1-14(13-17(21)22)7-8-16-19(4)11-6-10-18(2,3)15(19)9-12-20(16,5)23/h14-16,23H,6-13H2,1-5H3,(H,21,22)/p-1/t14-,15-,16+,19-,20+/m0/s1
SMILES:	C[C@@H](CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O)CC(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172637
PubChem CID:	11186394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17253868]
NPO3829	Euphorbia myrsinites	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[22192329]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	Flowers	São Paulo, Brazil.		PMID[32156350]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5143	Millettia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11973	Gymnothorax javanicus	Species	Muraenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2302	Sedum litoreum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7932	Ips confusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1509	Hippeastrum papilio	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3829	Euphorbia myrsinites	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25934	Diphasiastrum thyoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6480	Zanthoxylum fraxineum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26520	Wyethia mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8268	Croton laccifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6081	Limnocharis flava	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5918	Thermopsis dolichocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4007	Vicia amurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7057	Ptarmica ptarmicifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3423	Teucrium asiaticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1870	Polyporus dryadeus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5481	Fomes robiniae	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO275	Amphilophis odorata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2862	Dendrilla cavernosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO780	Senecio viscosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	80.0	%	PMID[518044]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[518044]

☑ 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 NPC19311 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	354
0.1-0.2	3323
0.2-0.3	14740
0.3-0.4	10685
0.4-0.5	6328
0.5-0.6	4975
0.6-0.7	1993
0.7-0.8	281
0.8-0.85	9
0.85-0.9	5
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230047
0.9677	High Similarity	NPC41542
0.8788	High Similarity	NPC196197
0.8615	High Similarity	NPC84562
0.8571	High Similarity	NPC104806
0.8462	Intermediate Similarity	NPC469791
0.8429	Intermediate Similarity	NPC212733
0.8358	Intermediate Similarity	NPC100917
0.8358	Intermediate Similarity	NPC469724
0.8358	Intermediate Similarity	NPC31187
0.8358	Intermediate Similarity	NPC281203
0.8333	Intermediate Similarity	NPC42060
0.831	Intermediate Similarity	NPC4209
0.8286	Intermediate Similarity	NPC280026
0.8286	Intermediate Similarity	NPC167702
0.8261	Intermediate Similarity	NPC478227
0.8261	Intermediate Similarity	NPC247195
0.8209	Intermediate Similarity	NPC472984
0.8209	Intermediate Similarity	NPC476928
0.8194	Intermediate Similarity	NPC207010
0.8194	Intermediate Similarity	NPC317913
0.8194	Intermediate Similarity	NPC112463
0.8194	Intermediate Similarity	NPC298168
0.8194	Intermediate Similarity	NPC143133
0.8143	Intermediate Similarity	NPC81759
0.8116	Intermediate Similarity	NPC108131
0.8088	Intermediate Similarity	NPC475977
0.8088	Intermediate Similarity	NPC470956
0.8082	Intermediate Similarity	NPC31031
0.8082	Intermediate Similarity	NPC224802
0.8082	Intermediate Similarity	NPC324700
0.8082	Intermediate Similarity	NPC80089
0.8082	Intermediate Similarity	NPC243594
0.8082	Intermediate Similarity	NPC171426
0.8082	Intermediate Similarity	NPC472608
0.8082	Intermediate Similarity	NPC34046
0.806	Intermediate Similarity	NPC477931
0.806	Intermediate Similarity	NPC268736
0.8028	Intermediate Similarity	NPC96759
0.8028	Intermediate Similarity	NPC162164
0.8	Intermediate Similarity	NPC58631
0.8	Intermediate Similarity	NPC48673
0.8	Intermediate Similarity	NPC20096
0.8	Intermediate Similarity	NPC476071
0.8	Intermediate Similarity	NPC280781
0.8	Intermediate Similarity	NPC48756
0.8	Intermediate Similarity	NPC12933
0.7973	Intermediate Similarity	NPC320144
0.7973	Intermediate Similarity	NPC80891
0.7973	Intermediate Similarity	NPC201276
0.7971	Intermediate Similarity	NPC476734
0.7971	Intermediate Similarity	NPC319671
0.7971	Intermediate Similarity	NPC469941
0.7971	Intermediate Similarity	NPC474962
0.7971	Intermediate Similarity	NPC252032
0.7945	Intermediate Similarity	NPC307865
0.7941	Intermediate Similarity	NPC478180
0.7941	Intermediate Similarity	NPC130459
0.7941	Intermediate Similarity	NPC474221
0.7937	Intermediate Similarity	NPC135438
0.7917	Intermediate Similarity	NPC39362
0.7887	Intermediate Similarity	NPC232112
0.7887	Intermediate Similarity	NPC109510
0.7887	Intermediate Similarity	NPC477229
0.7887	Intermediate Similarity	NPC282905
0.7887	Intermediate Similarity	NPC68426
0.7867	Intermediate Similarity	NPC261616
0.7857	Intermediate Similarity	NPC477929
0.7846	Intermediate Similarity	NPC478126
0.7838	Intermediate Similarity	NPC185465
0.7838	Intermediate Similarity	NPC329117
0.7838	Intermediate Similarity	NPC26029
0.7826	Intermediate Similarity	NPC478228
0.7826	Intermediate Similarity	NPC473225
0.7826	Intermediate Similarity	NPC36616
0.7826	Intermediate Similarity	NPC290445
0.7778	Intermediate Similarity	NPC46610
0.7778	Intermediate Similarity	NPC168511
0.7778	Intermediate Similarity	NPC55508
0.7778	Intermediate Similarity	NPC159325
0.7778	Intermediate Similarity	NPC38426
0.7778	Intermediate Similarity	NPC18819
0.7763	Intermediate Similarity	NPC474870
0.7763	Intermediate Similarity	NPC271572
0.7746	Intermediate Similarity	NPC469940
0.7746	Intermediate Similarity	NPC89310
0.7746	Intermediate Similarity	NPC472309
0.7746	Intermediate Similarity	NPC156277
0.7746	Intermediate Similarity	NPC58057
0.7746	Intermediate Similarity	NPC320549
0.7746	Intermediate Similarity	NPC151018
0.7733	Intermediate Similarity	NPC263951
0.7714	Intermediate Similarity	NPC6120
0.7714	Intermediate Similarity	NPC64466
0.7714	Intermediate Similarity	NPC131892
0.7714	Intermediate Similarity	NPC213178
0.7714	Intermediate Similarity	NPC327728
0.7703	Intermediate Similarity	NPC474433
0.7703	Intermediate Similarity	NPC477919
0.7703	Intermediate Similarity	NPC475031
0.7703	Intermediate Similarity	NPC23884
0.7703	Intermediate Similarity	NPC66105
0.7703	Intermediate Similarity	NPC180199
0.7692	Intermediate Similarity	NPC477434
0.7671	Intermediate Similarity	NPC174964
0.7671	Intermediate Similarity	NPC97534
0.7671	Intermediate Similarity	NPC267753
0.7671	Intermediate Similarity	NPC273366
0.7671	Intermediate Similarity	NPC195155
0.7671	Intermediate Similarity	NPC179858
0.7662	Intermediate Similarity	NPC289486
0.7662	Intermediate Similarity	NPC61107
0.7662	Intermediate Similarity	NPC30583
0.7662	Intermediate Similarity	NPC121121
0.7656	Intermediate Similarity	NPC236588
0.7639	Intermediate Similarity	NPC36310
0.7639	Intermediate Similarity	NPC177826
0.7632	Intermediate Similarity	NPC477851
0.7606	Intermediate Similarity	NPC163020
0.7606	Intermediate Similarity	NPC477850
0.7606	Intermediate Similarity	NPC91369
0.76	Intermediate Similarity	NPC199965
0.76	Intermediate Similarity	NPC476732
0.76	Intermediate Similarity	NPC321690
0.7595	Intermediate Similarity	NPC131350
0.7595	Intermediate Similarity	NPC477445
0.7581	Intermediate Similarity	NPC102336
0.7581	Intermediate Similarity	NPC36002
0.7571	Intermediate Similarity	NPC103647
0.7571	Intermediate Similarity	NPC260319
0.7571	Intermediate Similarity	NPC474954
0.7571	Intermediate Similarity	NPC2568
0.7571	Intermediate Similarity	NPC180777
0.7568	Intermediate Similarity	NPC20466
0.7568	Intermediate Similarity	NPC474020
0.7568	Intermediate Similarity	NPC475742
0.7568	Intermediate Similarity	NPC472486
0.7568	Intermediate Similarity	NPC472487
0.7568	Intermediate Similarity	NPC108840
0.7568	Intermediate Similarity	NPC5767
0.7536	Intermediate Similarity	NPC103734
0.7534	Intermediate Similarity	NPC130011
0.7534	Intermediate Similarity	NPC254340
0.7534	Intermediate Similarity	NPC74639
0.7534	Intermediate Similarity	NPC477930
0.7534	Intermediate Similarity	NPC255168
0.75	Intermediate Similarity	NPC73038
0.75	Intermediate Similarity	NPC231431
0.75	Intermediate Similarity	NPC197701
0.75	Intermediate Similarity	NPC73013
0.75	Intermediate Similarity	NPC72343
0.75	Intermediate Similarity	NPC472272
0.7468	Intermediate Similarity	NPC471044
0.7468	Intermediate Similarity	NPC219535
0.7468	Intermediate Similarity	NPC237938
0.7468	Intermediate Similarity	NPC473299
0.7468	Intermediate Similarity	NPC171789
0.7468	Intermediate Similarity	NPC473336
0.7468	Intermediate Similarity	NPC319909
0.7467	Intermediate Similarity	NPC221420
0.7467	Intermediate Similarity	NPC471151
0.7467	Intermediate Similarity	NPC477918
0.7467	Intermediate Similarity	NPC474404
0.7467	Intermediate Similarity	NPC472746
0.7465	Intermediate Similarity	NPC178541
0.7463	Intermediate Similarity	NPC306750
0.7432	Intermediate Similarity	NPC155441
0.7432	Intermediate Similarity	NPC159789
0.7432	Intermediate Similarity	NPC477934
0.7432	Intermediate Similarity	NPC186851
0.7432	Intermediate Similarity	NPC125767
0.7432	Intermediate Similarity	NPC21220
0.7432	Intermediate Similarity	NPC472311
0.7424	Intermediate Similarity	NPC95958
0.7403	Intermediate Similarity	NPC37038
0.7403	Intermediate Similarity	NPC472853
0.7397	Intermediate Similarity	NPC330659
0.7397	Intermediate Similarity	NPC161187
0.7397	Intermediate Similarity	NPC244708
0.7375	Intermediate Similarity	NPC264317
0.7375	Intermediate Similarity	NPC62572
0.7375	Intermediate Similarity	NPC224345
0.7375	Intermediate Similarity	NPC294438
0.7368	Intermediate Similarity	NPC179028
0.7368	Intermediate Similarity	NPC321514
0.7361	Intermediate Similarity	NPC235586
0.7342	Intermediate Similarity	NPC471037
0.7342	Intermediate Similarity	NPC243347
0.7333	Intermediate Similarity	NPC477932
0.7333	Intermediate Similarity	NPC89294
0.7333	Intermediate Similarity	NPC471046
0.7333	Intermediate Similarity	NPC477933
0.7333	Intermediate Similarity	NPC246445
0.7333	Intermediate Similarity	NPC324793
0.7333	Intermediate Similarity	NPC477878
0.7317	Intermediate Similarity	NPC471221
0.7317	Intermediate Similarity	NPC476379
0.7317	Intermediate Similarity	NPC476435
0.7313	Intermediate Similarity	NPC204173
0.7308	Intermediate Similarity	NPC50658

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 NPC19311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	3611
0.2-0.3	3427
0.3-0.4	1058
0.4-0.5	306
0.5-0.6	231
0.6-0.7	60
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8358	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD5360	Phase 3
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.831	Intermediate Similarity	NPD6117	Approved
0.8286	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6116	Phase 1
0.8082	Intermediate Similarity	NPD6697	Approved
0.8082	Intermediate Similarity	NPD6118	Approved
0.8082	Intermediate Similarity	NPD6115	Approved
0.8082	Intermediate Similarity	NPD6114	Approved
0.8	Intermediate Similarity	NPD6081	Approved
0.7746	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4758	Discontinued
0.7714	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3702	Approved
0.7647	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3703	Phase 2
0.7375	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5364	Discontinued
0.7361	Intermediate Similarity	NPD4245	Approved
0.7361	Intermediate Similarity	NPD4789	Approved
0.7361	Intermediate Similarity	NPD4244	Approved
0.726	Intermediate Similarity	NPD5777	Approved
0.7222	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD634	Phase 3
0.6923	Remote Similarity	NPD3671	Phase 1
0.6923	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3186	Phase 1
0.686	Remote Similarity	NPD7515	Phase 2
0.686	Remote Similarity	NPD8034	Phase 2
0.686	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD3198	Approved
0.6588	Remote Similarity	NPD3573	Approved
0.6506	Remote Similarity	NPD4788	Approved
0.65	Remote Similarity	NPD3617	Approved
0.65	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7902	Approved
0.6471	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD386	Approved
0.6452	Remote Similarity	NPD388	Approved
0.6447	Remote Similarity	NPD4787	Phase 1
0.6437	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6386	Remote Similarity	NPD4223	Phase 3
0.6386	Remote Similarity	NPD4221	Approved
0.6386	Remote Similarity	NPD3667	Approved
0.6353	Remote Similarity	NPD5329	Approved
0.6344	Remote Similarity	NPD8418	Phase 2
0.6333	Remote Similarity	NPD2270	Approved
0.6316	Remote Similarity	NPD3725	Approved
0.6316	Remote Similarity	NPD3726	Approved
0.6301	Remote Similarity	NPD7909	Approved
0.6292	Remote Similarity	NPD6079	Approved
0.6279	Remote Similarity	NPD6098	Approved
0.6265	Remote Similarity	NPD4692	Approved
0.6265	Remote Similarity	NPD4139	Approved
0.6235	Remote Similarity	NPD4197	Approved
0.6222	Remote Similarity	NPD4202	Approved
0.6186	Remote Similarity	NPD6675	Approved
0.6186	Remote Similarity	NPD7128	Approved
0.6186	Remote Similarity	NPD5739	Approved
0.6186	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7900	Approved
0.6154	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4695	Discontinued
0.6129	Remote Similarity	NPD6084	Phase 2
0.6129	Remote Similarity	NPD6083	Phase 2
0.6118	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3669	Approved
0.6111	Remote Similarity	NPD9656	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6094	Remote Similarity	NPD384	Approved
0.6094	Remote Similarity	NPD385	Approved
0.6092	Remote Similarity	NPD7146	Approved
0.6092	Remote Similarity	NPD7521	Approved
0.6092	Remote Similarity	NPD4690	Approved
0.6092	Remote Similarity	NPD4693	Phase 3
0.6092	Remote Similarity	NPD4519	Discontinued
0.6092	Remote Similarity	NPD4138	Approved
0.6092	Remote Similarity	NPD4689	Approved
0.6092	Remote Similarity	NPD7334	Approved
0.6092	Remote Similarity	NPD4623	Approved
0.6092	Remote Similarity	NPD6409	Approved
0.6092	Remote Similarity	NPD5330	Approved
0.6092	Remote Similarity	NPD6684	Approved
0.6092	Remote Similarity	NPD5205	Approved
0.6092	Remote Similarity	NPD4688	Approved
0.6087	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1780	Approved
0.6071	Remote Similarity	NPD1779	Approved
0.6067	Remote Similarity	NPD6080	Approved
0.6067	Remote Similarity	NPD6904	Approved
0.6067	Remote Similarity	NPD6673	Approved
0.6064	Remote Similarity	NPD7638	Approved
0.6061	Remote Similarity	NPD7320	Approved
0.6061	Remote Similarity	NPD6899	Approved
0.6061	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6881	Approved
0.6047	Remote Similarity	NPD3665	Phase 1
0.6047	Remote Similarity	NPD3133	Approved
0.6047	Remote Similarity	NPD3666	Approved
0.6032	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD9448	Phase 2
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD633	Phase 3
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD2266	Phase 2
0.6	Remote Similarity	NPD77	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD9450	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5978	Remote Similarity	NPD6001	Approved
0.597	Remote Similarity	NPD9638	Phase 2
0.596	Remote Similarity	NPD5701	Approved
0.596	Remote Similarity	NPD5697	Approved
0.5957	Remote Similarity	NPD4755	Approved
0.5955	Remote Similarity	NPD5737	Approved
0.5955	Remote Similarity	NPD5208	Approved
0.5955	Remote Similarity	NPD6672	Approved
0.5955	Remote Similarity	NPD6903	Approved
0.5955	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7525	Registered
0.5941	Remote Similarity	NPD7290	Approved
0.5941	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD7102	Approved
0.5921	Remote Similarity	NPD375	Phase 2
0.5915	Remote Similarity	NPD9439	Approved
0.5915	Remote Similarity	NPD9438	Approved
0.5914	Remote Similarity	NPD5695	Phase 3
0.5909	Remote Similarity	NPD5280	Approved
0.5909	Remote Similarity	NPD4694	Approved
0.5909	Remote Similarity	NPD5690	Phase 2
0.59	Remote Similarity	NPD6011	Approved
0.5895	Remote Similarity	NPD5696	Approved
0.5889	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD6847	Approved
0.5882	Remote Similarity	NPD6617	Approved
0.5882	Remote Similarity	NPD8130	Phase 1
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6650	Approved
0.5876	Remote Similarity	NPD7632	Discontinued
0.5862	Remote Similarity	NPD3668	Phase 3
0.5851	Remote Similarity	NPD5221	Approved
0.5851	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4697	Phase 3
0.5851	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6014	Approved
0.5842	Remote Similarity	NPD6013	Approved
0.5842	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD3206	Approved
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5833	Remote Similarity	NPD4700	Approved
0.5825	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD8297	Approved
0.5814	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5173	Approved
0.5784	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5223	Approved
0.5773	Remote Similarity	NPD1700	Approved
0.5769	Remote Similarity	NPD229	Approved
0.5769	Remote Similarity	NPD6705	Phase 1
0.5765	Remote Similarity	NPD6928	Phase 2
0.5761	Remote Similarity	NPD6050	Approved
0.5761	Remote Similarity	NPD6411	Approved
0.5761	Remote Similarity	NPD5693	Phase 1
0.575	Remote Similarity	NPD4243	Approved
0.5738	Remote Similarity	NPD9655	Approved
0.5732	Remote Similarity	NPD2257	Approved
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD4238	Approved
0.5667	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD371	Approved
0.5657	Remote Similarity	NPD4754	Approved
0.5657	Remote Similarity	NPD5175	Approved
0.5657	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD5692	Phase 3
0.5652	Remote Similarity	NPD5207	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