NPASS Compound

Structure

CID135438 OpenBabel06191715492D 22 23 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 0.8660 3.5000 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 4.5000 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 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 -1.0000 -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 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 1 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.29
Volume:	354.944
LogP:	4.838
LogD:	4.186
LogS:	-4.942
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	4.116
Fsp3:	1.0
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:	-4.56
MDCK Permeability:	1.612021151231602e-05
Pgp-inhibitor:	0.776
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.59

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	91.61980438232422%
Volume Distribution (VD):	1.415
Pgp-substrate:	5.988403797149658%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.686
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	8.568
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.905
Carcinogencity:	0.086
Eye Corrosion:	0.986
Eye Irritation:	0.846
Respiratory Toxicity:	0.869

Download Data

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

Natural Product: NPC135438

Natural Product ID:	NPC135438
*Common Name:**	Labdanediol
IUPAC Name:	(1R,2R,4aS,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:	Labdanediol
Standard InCHIKey:	MCHQEVJMCLOQAZ-VBYALHQYSA-N
Standard InCHI:	InChI=1S/C20H38O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h15-17,21-22H,6-14H2,1-5H3/t15-,16-,17+,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)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172098
PubChem CID:	11130717
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]
NPO40306	Psiadia arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30943031]
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]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1509	Hippeastrum papilio	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7932	Ips confusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25934	Diphasiastrum thyoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26520	Wyethia mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3829	Euphorbia myrsinites	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]
NPO6480	Zanthoxylum fraxineum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4007	Vicia amurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8268	Croton laccifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5918	Thermopsis dolichocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3423	Teucrium asiaticum	Species	Lamiaceae	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]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1870	Polyporus dryadeus	Species	Polyporaceae	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]
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5143	Millettia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2302	Sedum litoreum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11973	Gymnothorax javanicus	Species	Muraenidae	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	3
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	40.0	%	PMID[469495]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	25000.0	nM	PMID[469495]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15000.0	nM	PMID[469495]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	22200.0	nM	PMID[469496]

☑ 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 NPC135438 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	399
0.1-0.2	4437
0.2-0.3	18066
0.3-0.4	8849
0.4-0.5	5621
0.5-0.6	3856
0.6-0.7	1185
0.7-0.8	244
0.8-0.85	26
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC236588
0.8833	High Similarity	NPC80463
0.8833	High Similarity	NPC260116
0.8571	High Similarity	NPC471269
0.8548	High Similarity	NPC48079
0.8548	High Similarity	NPC476928
0.8545	High Similarity	NPC36002
0.8545	High Similarity	NPC102336
0.85	High Similarity	NPC114891
0.85	High Similarity	NPC290791
0.85	High Similarity	NPC292419
0.8448	Intermediate Similarity	NPC47663
0.8413	Intermediate Similarity	NPC472741
0.8413	Intermediate Similarity	NPC475893
0.8413	Intermediate Similarity	NPC2648
0.8393	Intermediate Similarity	NPC53209
0.8387	Intermediate Similarity	NPC142712
0.8387	Intermediate Similarity	NPC44122
0.8361	Intermediate Similarity	NPC118937
0.8361	Intermediate Similarity	NPC281540
0.8361	Intermediate Similarity	NPC159654
0.8361	Intermediate Similarity	NPC167995
0.8333	Intermediate Similarity	NPC148174
0.8333	Intermediate Similarity	NPC71460
0.8333	Intermediate Similarity	NPC218585
0.8305	Intermediate Similarity	NPC95958
0.8281	Intermediate Similarity	NPC107919
0.8281	Intermediate Similarity	NPC241085
0.8281	Intermediate Similarity	NPC129829
0.8281	Intermediate Similarity	NPC299948
0.8281	Intermediate Similarity	NPC254037
0.8281	Intermediate Similarity	NPC470833
0.8281	Intermediate Similarity	NPC66407
0.8281	Intermediate Similarity	NPC210323
0.8281	Intermediate Similarity	NPC470830
0.8254	Intermediate Similarity	NPC204233
0.8254	Intermediate Similarity	NPC475884
0.8254	Intermediate Similarity	NPC473230
0.8254	Intermediate Similarity	NPC63190
0.8226	Intermediate Similarity	NPC41577
0.8226	Intermediate Similarity	NPC473276
0.8226	Intermediate Similarity	NPC474380
0.8154	Intermediate Similarity	NPC282454
0.8154	Intermediate Similarity	NPC192192
0.8154	Intermediate Similarity	NPC231945
0.8136	Intermediate Similarity	NPC476735
0.8125	Intermediate Similarity	NPC469987
0.8125	Intermediate Similarity	NPC474756
0.8113	Intermediate Similarity	NPC14552
0.8065	Intermediate Similarity	NPC69149
0.8065	Intermediate Similarity	NPC101128
0.8033	Intermediate Similarity	NPC95804
0.8033	Intermediate Similarity	NPC185547
0.803	Intermediate Similarity	NPC157777
0.803	Intermediate Similarity	NPC252182
0.803	Intermediate Similarity	NPC109457
0.803	Intermediate Similarity	NPC187471
0.803	Intermediate Similarity	NPC195530
0.803	Intermediate Similarity	NPC131506
0.803	Intermediate Similarity	NPC473279
0.803	Intermediate Similarity	NPC1340
0.803	Intermediate Similarity	NPC167706
0.803	Intermediate Similarity	NPC100586
0.803	Intermediate Similarity	NPC470071
0.803	Intermediate Similarity	NPC127094
0.803	Intermediate Similarity	NPC157422
0.8	Intermediate Similarity	NPC477820
0.7969	Intermediate Similarity	NPC41542
0.7969	Intermediate Similarity	NPC269077
0.7969	Intermediate Similarity	NPC253303
0.7969	Intermediate Similarity	NPC139207
0.7969	Intermediate Similarity	NPC472984
0.7969	Intermediate Similarity	NPC185874
0.7937	Intermediate Similarity	NPC243469
0.7937	Intermediate Similarity	NPC230047
0.7937	Intermediate Similarity	NPC258595
0.7937	Intermediate Similarity	NPC472946
0.7937	Intermediate Similarity	NPC475943
0.7937	Intermediate Similarity	NPC19311
0.7937	Intermediate Similarity	NPC190827
0.791	Intermediate Similarity	NPC473238
0.791	Intermediate Similarity	NPC472341
0.791	Intermediate Similarity	NPC153719
0.791	Intermediate Similarity	NPC253805
0.791	Intermediate Similarity	NPC81759
0.7903	Intermediate Similarity	NPC236099
0.7903	Intermediate Similarity	NPC209686
0.7903	Intermediate Similarity	NPC249078
0.7879	Intermediate Similarity	NPC232925
0.7879	Intermediate Similarity	NPC251201
0.7879	Intermediate Similarity	NPC63588
0.7846	Intermediate Similarity	NPC244790
0.7833	Intermediate Similarity	NPC87296
0.7833	Intermediate Similarity	NPC215671
0.7833	Intermediate Similarity	NPC475515
0.7818	Intermediate Similarity	NPC316035
0.7797	Intermediate Similarity	NPC3025
0.7794	Intermediate Similarity	NPC475793
0.7794	Intermediate Similarity	NPC237510
0.7794	Intermediate Similarity	NPC304499
0.7794	Intermediate Similarity	NPC10476
0.7794	Intermediate Similarity	NPC201048
0.7794	Intermediate Similarity	NPC192501
0.7794	Intermediate Similarity	NPC228994
0.7794	Intermediate Similarity	NPC476366
0.7794	Intermediate Similarity	NPC477508
0.7778	Intermediate Similarity	NPC198540
0.7778	Intermediate Similarity	NPC94897
0.7778	Intermediate Similarity	NPC147343
0.7778	Intermediate Similarity	NPC176309
0.7778	Intermediate Similarity	NPC287550
0.7778	Intermediate Similarity	NPC144650
0.7778	Intermediate Similarity	NPC84030
0.7778	Intermediate Similarity	NPC223468
0.7761	Intermediate Similarity	NPC478103
0.7761	Intermediate Similarity	NPC8004
0.7761	Intermediate Similarity	NPC127283
0.7727	Intermediate Similarity	NPC9942
0.7692	Intermediate Similarity	NPC101307
0.7692	Intermediate Similarity	NPC88454
0.7692	Intermediate Similarity	NPC117607
0.7681	Intermediate Similarity	NPC196136
0.7681	Intermediate Similarity	NPC317242
0.7681	Intermediate Similarity	NPC91387
0.7681	Intermediate Similarity	NPC158208
0.7681	Intermediate Similarity	NPC3403
0.7681	Intermediate Similarity	NPC472952
0.7681	Intermediate Similarity	NPC270306
0.7681	Intermediate Similarity	NPC472950
0.7681	Intermediate Similarity	NPC243027
0.7681	Intermediate Similarity	NPC231680
0.7656	Intermediate Similarity	NPC172613
0.7656	Intermediate Similarity	NPC282619
0.7656	Intermediate Similarity	NPC208198
0.7656	Intermediate Similarity	NPC2728
0.7656	Intermediate Similarity	NPC60837
0.7656	Intermediate Similarity	NPC11555
0.7656	Intermediate Similarity	NPC64123
0.7647	Intermediate Similarity	NPC232112
0.7647	Intermediate Similarity	NPC470610
0.7647	Intermediate Similarity	NPC477229
0.7647	Intermediate Similarity	NPC211009
0.7647	Intermediate Similarity	NPC68426
0.7647	Intermediate Similarity	NPC282905
0.7612	Intermediate Similarity	NPC45296
0.7576	Intermediate Similarity	NPC276616
0.7576	Intermediate Similarity	NPC478228
0.7576	Intermediate Similarity	NPC245795
0.7571	Intermediate Similarity	NPC91573
0.7571	Intermediate Similarity	NPC470145
0.7571	Intermediate Similarity	NPC63958
0.7571	Intermediate Similarity	NPC163597
0.7571	Intermediate Similarity	NPC470749
0.7544	Intermediate Similarity	NPC307022
0.7541	Intermediate Similarity	NPC474769
0.7541	Intermediate Similarity	NPC162685
0.7541	Intermediate Similarity	NPC189290
0.7538	Intermediate Similarity	NPC473929
0.7538	Intermediate Similarity	NPC476406
0.7536	Intermediate Similarity	NPC159325
0.7536	Intermediate Similarity	NPC476736
0.7536	Intermediate Similarity	NPC48795
0.7536	Intermediate Similarity	NPC475458
0.7536	Intermediate Similarity	NPC74639
0.7536	Intermediate Similarity	NPC478130
0.7536	Intermediate Similarity	NPC472503
0.7536	Intermediate Similarity	NPC168511
0.7536	Intermediate Similarity	NPC308440
0.75	Intermediate Similarity	NPC68656
0.75	Intermediate Similarity	NPC151018
0.75	Intermediate Similarity	NPC111234
0.75	Intermediate Similarity	NPC89310
0.75	Intermediate Similarity	NPC320549
0.75	Intermediate Similarity	NPC301226
0.75	Intermediate Similarity	NPC156277
0.75	Intermediate Similarity	NPC58057
0.7465	Intermediate Similarity	NPC105208
0.7465	Intermediate Similarity	NPC474574
0.7465	Intermediate Similarity	NPC133596
0.7465	Intermediate Similarity	NPC128951
0.7465	Intermediate Similarity	NPC23884
0.7465	Intermediate Similarity	NPC470711
0.7465	Intermediate Similarity	NPC475031
0.7465	Intermediate Similarity	NPC64081
0.7465	Intermediate Similarity	NPC185915
0.7465	Intermediate Similarity	NPC11907
0.7465	Intermediate Similarity	NPC476233
0.7465	Intermediate Similarity	NPC302578
0.7465	Intermediate Similarity	NPC192046
0.7465	Intermediate Similarity	NPC477227
0.7465	Intermediate Similarity	NPC470758
0.7465	Intermediate Similarity	NPC169994
0.7463	Intermediate Similarity	NPC213178
0.7463	Intermediate Similarity	NPC327728
0.7463	Intermediate Similarity	NPC131892
0.7463	Intermediate Similarity	NPC6120
0.7458	Intermediate Similarity	NPC32222
0.7458	Intermediate Similarity	NPC202146
0.7429	Intermediate Similarity	NPC231256
0.7429	Intermediate Similarity	NPC273366

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 NPC135438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	455
0.1-0.2	4388
0.2-0.3	3074
0.3-0.4	745
0.4-0.5	250
0.5-0.6	187
0.6-0.7	40
0.7-0.8	11
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
0.8281	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4787	Phase 1
0.7778	Intermediate Similarity	NPD384	Approved
0.7778	Intermediate Similarity	NPD385	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6117	Approved
0.7313	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5360	Phase 3
0.7286	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD388	Approved
0.7273	Intermediate Similarity	NPD386	Approved
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7183	Intermediate Similarity	NPD3703	Phase 2
0.7162	Intermediate Similarity	NPD7525	Registered
0.7123	Intermediate Similarity	NPD6697	Approved
0.7123	Intermediate Similarity	NPD6115	Approved
0.7123	Intermediate Similarity	NPD6118	Approved
0.7123	Intermediate Similarity	NPD6114	Approved
0.7101	Intermediate Similarity	NPD4245	Approved
0.7101	Intermediate Similarity	NPD4244	Approved
0.7101	Intermediate Similarity	NPD4789	Approved
0.7059	Intermediate Similarity	NPD6705	Phase 1
0.7027	Intermediate Similarity	NPD7645	Phase 2
0.697	Remote Similarity	NPD371	Approved
0.6957	Remote Similarity	NPD3698	Phase 2
0.6761	Remote Similarity	NPD4758	Discontinued
0.6712	Remote Similarity	NPD7339	Approved
0.6712	Remote Similarity	NPD6942	Approved
0.6711	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD3671	Phase 1
0.6622	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6924	Approved
0.6575	Remote Similarity	NPD6926	Approved
0.6522	Remote Similarity	NPD4224	Phase 2
0.65	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4748	Discontinued
0.6486	Remote Similarity	NPD3702	Approved
0.6447	Remote Similarity	NPD5364	Discontinued
0.64	Remote Similarity	NPD6933	Approved
0.6351	Remote Similarity	NPD1810	Approved
0.6351	Remote Similarity	NPD1811	Approved
0.6316	Remote Similarity	NPD367	Approved
0.6301	Remote Similarity	NPD4243	Approved
0.6301	Remote Similarity	NPD6081	Approved
0.6282	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD4788	Approved
0.622	Remote Similarity	NPD3618	Phase 1
0.619	Remote Similarity	NPD5328	Approved
0.6173	Remote Similarity	NPD4786	Approved
0.6133	Remote Similarity	NPD4784	Approved
0.6133	Remote Similarity	NPD4785	Approved
0.6125	Remote Similarity	NPD3667	Approved
0.6118	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6700	Approved
0.6081	Remote Similarity	NPD5777	Approved
0.6081	Remote Similarity	NPD7152	Approved
0.6081	Remote Similarity	NPD7151	Approved
0.6081	Remote Similarity	NPD7150	Approved
0.6076	Remote Similarity	NPD6930	Phase 2
0.6076	Remote Similarity	NPD6931	Approved
0.6053	Remote Similarity	NPD8264	Approved
0.6047	Remote Similarity	NPD6079	Approved
0.6047	Remote Similarity	NPD7515	Phase 2
0.6047	Remote Similarity	NPD6703	Approved
0.6047	Remote Similarity	NPD6702	Approved
0.6027	Remote Similarity	NPD6922	Approved
0.6027	Remote Similarity	NPD6923	Approved
0.5977	Remote Similarity	NPD4202	Approved
0.5952	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6929	Approved
0.5946	Remote Similarity	NPD2687	Approved
0.5946	Remote Similarity	NPD2686	Approved
0.5946	Remote Similarity	NPD7144	Approved
0.5946	Remote Similarity	NPD2254	Approved
0.5946	Remote Similarity	NPD7143	Approved
0.5897	Remote Similarity	NPD6932	Approved
0.5862	Remote Similarity	NPD8035	Phase 2
0.5862	Remote Similarity	NPD8034	Phase 2
0.5854	Remote Similarity	NPD6695	Phase 3
0.5846	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD4190	Phase 3
0.5844	Remote Similarity	NPD5275	Approved
0.5823	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD8171	Discontinued
0.5783	Remote Similarity	NPD3665	Phase 1
0.5783	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD3666	Approved
0.5783	Remote Similarity	NPD3133	Approved
0.575	Remote Similarity	NPD6683	Phase 2
0.575	Remote Similarity	NPD4195	Approved
0.5733	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD6893	Approved
0.5714	Remote Similarity	NPD7919	Phase 3
0.5714	Remote Similarity	NPD7920	Phase 3
0.5714	Remote Similarity	NPD4755	Approved
0.5696	Remote Similarity	NPD6925	Approved
0.5696	Remote Similarity	NPD5776	Phase 2
0.5679	Remote Similarity	NPD7332	Phase 2
0.5679	Remote Similarity	NPD7514	Phase 3
0.5663	Remote Similarity	NPD3669	Approved
0.5663	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.566	Remote Similarity	NPD2272	Approved
0.566	Remote Similarity	NPD5383	Approved
0.5652	Remote Similarity	NPD3198	Approved
0.5652	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD8088	Phase 1
0.5647	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD8308	Discontinued
0.5632	Remote Similarity	NPD4753	Phase 2
0.5625	Remote Similarity	NPD3617	Approved
0.5625	Remote Similarity	NPD7145	Approved
0.561	Remote Similarity	NPD6898	Phase 1
0.5606	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4697	Phase 3
0.5604	Remote Similarity	NPD5221	Approved
0.5604	Remote Similarity	NPD5222	Approved
0.5604	Remote Similarity	NPD5220	Clinical (unspecified phase)

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