NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.22
Volume:	326.919
LogP:	6.156
LogD:	3.69
LogS:	-4.973
# Rotatable Bonds:	13
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	2.589
Fsp3:	0.611
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:	-4.631
MDCK Permeability:	5.262751528789522e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	97.11875915527344%
Volume Distribution (VD):	0.594
Pgp-substrate:	2.336357831954956%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	4.877
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.006
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.965
Carcinogencity:	0.106
Eye Corrosion:	0.987
Eye Irritation:	0.987
Respiratory Toxicity:	0.674

Download Data

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

Natural Product: NPC1813

Natural Product ID:	NPC1813
*Common Name:**	Octadeca-9,12,15-Trienoic Acid
IUPAC Name:	octadeca-9,12,15-trienoic acid
Synonyms:
Standard InCHIKey:	DTOSIQBPPRVQHS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)
SMILES:	CCC=CCC=CCC=CCCCCCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3560296
PubChem CID:	860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12405	Descurainia sophia	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	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	10

Activity Type	# Activity
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	n.a.	20000.0	nM	PMID[458572]
NPT2	Others	Unspecified		IC50	n.a.	10000.0	nM	PMID[458572]

☑ 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 NPC1813 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	138
0.1-0.2	2852
0.2-0.3	16555
0.3-0.4	12552
0.4-0.5	7039
0.5-0.6	2832
0.6-0.7	529
0.7-0.8	111
0.8-0.85	26
0.85-0.9	22
0.9-0.95	15
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36061
1.0	High Similarity	NPC294548
1.0	High Similarity	NPC139029
0.98	High Similarity	NPC424
0.98	High Similarity	NPC88966
0.98	High Similarity	NPC87564
0.98	High Similarity	NPC6095
0.98	High Similarity	NPC25417
0.98	High Similarity	NPC154245
0.98	High Similarity	NPC290563
0.98	High Similarity	NPC261831
0.98	High Similarity	NPC85813
0.98	High Similarity	NPC32467
0.98	High Similarity	NPC281972
0.9796	High Similarity	NPC281245
0.96	High Similarity	NPC321062
0.96	High Similarity	NPC70387
0.9423	High Similarity	NPC179764
0.9423	High Similarity	NPC187777
0.9423	High Similarity	NPC477201
0.9423	High Similarity	NPC18951
0.94	High Similarity	NPC92114
0.9388	High Similarity	NPC224227
0.9245	High Similarity	NPC225929
0.9231	High Similarity	NPC473863
0.9231	High Similarity	NPC274290
0.9231	High Similarity	NPC54766
0.92	High Similarity	NPC262968
0.9184	High Similarity	NPC5413
0.9184	High Similarity	NPC149821
0.9	High Similarity	NPC59051
0.898	High Similarity	NPC180534
0.898	High Similarity	NPC207292
0.8909	High Similarity	NPC274927
0.8909	High Similarity	NPC106851
0.8846	High Similarity	NPC309606
0.8846	High Similarity	NPC139545
0.8846	High Similarity	NPC39633
0.875	High Similarity	NPC122521
0.875	High Similarity	NPC251042
0.875	High Similarity	NPC235242
0.875	High Similarity	NPC243532
0.875	High Similarity	NPC174447
0.8654	High Similarity	NPC18357
0.86	High Similarity	NPC91495
0.8596	High Similarity	NPC201939
0.8596	High Similarity	NPC40082
0.8571	High Similarity	NPC117572
0.8519	High Similarity	NPC10316
0.8519	High Similarity	NPC223677
0.8519	High Similarity	NPC28779
0.8519	High Similarity	NPC128061
0.8519	High Similarity	NPC228473
0.8519	High Similarity	NPC200845
0.8491	Intermediate Similarity	NPC71761
0.8462	Intermediate Similarity	NPC28205
0.8462	Intermediate Similarity	NPC284212
0.8462	Intermediate Similarity	NPC470412
0.8462	Intermediate Similarity	NPC470410
0.8393	Intermediate Similarity	NPC267817
0.8393	Intermediate Similarity	NPC34416
0.8333	Intermediate Similarity	NPC87394
0.8305	Intermediate Similarity	NPC328089
0.8305	Intermediate Similarity	NPC68343
0.8305	Intermediate Similarity	NPC470320
0.8276	Intermediate Similarity	NPC174560
0.8276	Intermediate Similarity	NPC125312
0.8235	Intermediate Similarity	NPC216130
0.8182	Intermediate Similarity	NPC52264
0.8167	Intermediate Similarity	NPC245947
0.8167	Intermediate Similarity	NPC326268
0.8167	Intermediate Similarity	NPC136164
0.8167	Intermediate Similarity	NPC255863
0.8167	Intermediate Similarity	NPC318420
0.8113	Intermediate Similarity	NPC48162
0.8036	Intermediate Similarity	NPC325977
0.8	Intermediate Similarity	NPC137538
0.8	Intermediate Similarity	NPC226592
0.7966	Intermediate Similarity	NPC328776
0.7966	Intermediate Similarity	NPC320305
0.7966	Intermediate Similarity	NPC321838
0.7963	Intermediate Similarity	NPC161366
0.7903	Intermediate Similarity	NPC148192
0.7903	Intermediate Similarity	NPC26500
0.7903	Intermediate Similarity	NPC271921
0.7903	Intermediate Similarity	NPC127091
0.7903	Intermediate Similarity	NPC104537
0.7903	Intermediate Similarity	NPC330426
0.7903	Intermediate Similarity	NPC22101
0.7903	Intermediate Similarity	NPC99619
0.7857	Intermediate Similarity	NPC45626
0.78	Intermediate Similarity	NPC270796
0.7797	Intermediate Similarity	NPC143857
0.7797	Intermediate Similarity	NPC229252
0.7778	Intermediate Similarity	NPC48218
0.7778	Intermediate Similarity	NPC324981
0.7778	Intermediate Similarity	NPC476614
0.7778	Intermediate Similarity	NPC141481
0.7778	Intermediate Similarity	NPC473559
0.7759	Intermediate Similarity	NPC329819
0.7736	Intermediate Similarity	NPC207815
0.7705	Intermediate Similarity	NPC234767
0.7692	Intermediate Similarity	NPC42304
0.7679	Intermediate Similarity	NPC322461
0.7667	Intermediate Similarity	NPC477829
0.7656	Intermediate Similarity	NPC317583
0.7656	Intermediate Similarity	NPC143396
0.7636	Intermediate Similarity	NPC129458
0.7627	Intermediate Similarity	NPC329550
0.7619	Intermediate Similarity	NPC473829
0.7619	Intermediate Similarity	NPC475443
0.7619	Intermediate Similarity	NPC60120
0.7541	Intermediate Similarity	NPC477707
0.7541	Intermediate Similarity	NPC54925
0.7538	Intermediate Similarity	NPC476660
0.7538	Intermediate Similarity	NPC42526
0.75	Intermediate Similarity	NPC53302
0.75	Intermediate Similarity	NPC10081
0.75	Intermediate Similarity	NPC225066
0.75	Intermediate Similarity	NPC328311
0.75	Intermediate Similarity	NPC327112
0.746	Intermediate Similarity	NPC308294
0.746	Intermediate Similarity	NPC142423
0.7455	Intermediate Similarity	NPC477458
0.7414	Intermediate Similarity	NPC327388
0.7407	Intermediate Similarity	NPC163345
0.74	Intermediate Similarity	NPC209970
0.74	Intermediate Similarity	NPC196924
0.74	Intermediate Similarity	NPC307783
0.74	Intermediate Similarity	NPC216630
0.74	Intermediate Similarity	NPC149184
0.74	Intermediate Similarity	NPC171736
0.7385	Intermediate Similarity	NPC473772
0.7347	Intermediate Similarity	NPC279026
0.7347	Intermediate Similarity	NPC301585
0.7347	Intermediate Similarity	NPC154186
0.7347	Intermediate Similarity	NPC113928
0.7347	Intermediate Similarity	NPC301696
0.7347	Intermediate Similarity	NPC261080
0.7347	Intermediate Similarity	NPC201844
0.7347	Intermediate Similarity	NPC14227
0.7321	Intermediate Similarity	NPC303765
0.7288	Intermediate Similarity	NPC211752
0.7288	Intermediate Similarity	NPC323597
0.7288	Intermediate Similarity	NPC323498
0.7288	Intermediate Similarity	NPC323436
0.7258	Intermediate Similarity	NPC477830
0.7255	Intermediate Similarity	NPC67462
0.7241	Intermediate Similarity	NPC474672
0.7241	Intermediate Similarity	NPC477984
0.7206	Intermediate Similarity	NPC3753
0.7206	Intermediate Similarity	NPC251970
0.7206	Intermediate Similarity	NPC183503
0.7206	Intermediate Similarity	NPC227396
0.7206	Intermediate Similarity	NPC474321
0.7206	Intermediate Similarity	NPC237591
0.7206	Intermediate Similarity	NPC241854
0.7206	Intermediate Similarity	NPC161923
0.7206	Intermediate Similarity	NPC283908
0.7206	Intermediate Similarity	NPC55527
0.7206	Intermediate Similarity	NPC476046
0.7206	Intermediate Similarity	NPC103958
0.717	Intermediate Similarity	NPC239754
0.717	Intermediate Similarity	NPC76976
0.7167	Intermediate Similarity	NPC469373
0.7164	Intermediate Similarity	NPC288667
0.7164	Intermediate Similarity	NPC320119
0.7164	Intermediate Similarity	NPC320669
0.7164	Intermediate Similarity	NPC318814
0.7164	Intermediate Similarity	NPC160817
0.7143	Intermediate Similarity	NPC178586
0.7115	Intermediate Similarity	NPC252978
0.7115	Intermediate Similarity	NPC74845
0.7115	Intermediate Similarity	NPC19305
0.7115	Intermediate Similarity	NPC255837
0.7101	Intermediate Similarity	NPC476844
0.7101	Intermediate Similarity	NPC192540
0.7101	Intermediate Similarity	NPC279666
0.7097	Intermediate Similarity	NPC113293
0.7077	Intermediate Similarity	NPC472875
0.7059	Intermediate Similarity	NPC325627
0.7059	Intermediate Similarity	NPC326024
0.7049	Intermediate Similarity	NPC329249
0.7037	Intermediate Similarity	NPC110234
0.7037	Intermediate Similarity	NPC163751
0.7037	Intermediate Similarity	NPC44363
0.7031	Intermediate Similarity	NPC320642
0.7031	Intermediate Similarity	NPC476657
0.7031	Intermediate Similarity	NPC476654
0.7031	Intermediate Similarity	NPC317881
0.7031	Intermediate Similarity	NPC476655
0.7031	Intermediate Similarity	NPC323045
0.7018	Intermediate Similarity	NPC310746
0.7018	Intermediate Similarity	NPC216407
0.7015	Intermediate Similarity	NPC67183
0.7	Intermediate Similarity	NPC469514
0.7	Intermediate Similarity	NPC69143
0.7	Intermediate Similarity	NPC214610
0.7	Intermediate Similarity	NPC118968
0.7	Intermediate Similarity	NPC281230

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 NPC1813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	3248
0.2-0.3	3837
0.3-0.4	1378
0.4-0.5	424
0.5-0.6	101
0.6-0.7	27
0.7-0.8	7
0.8-0.85	3
0.85-0.9	3
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3172	Approved
0.98	High Similarity	NPD3194	Approved
0.98	High Similarity	NPD3196	Approved
0.98	High Similarity	NPD4266	Approved
0.98	High Similarity	NPD3195	Phase 2
0.92	High Similarity	NPD29	Approved
0.92	High Similarity	NPD28	Approved
0.9184	High Similarity	NPD3173	Approved
0.898	High Similarity	NPD622	Approved
0.8571	High Similarity	NPD3174	Discontinued
0.8571	High Similarity	NPD4222	Approved
0.8305	Intermediate Similarity	NPD3197	Phase 1
0.82	Intermediate Similarity	NPD39	Approved
0.78	Intermediate Similarity	NPD5326	Phase 3
0.75	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2270	Approved
0.7347	Intermediate Similarity	NPD9448	Phase 2
0.7347	Intermediate Similarity	NPD633	Phase 3
0.7222	Intermediate Similarity	NPD5343	Approved
0.7	Intermediate Similarity	NPD9655	Approved
0.6984	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7331	Phase 2
0.6818	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3732	Approved
0.68	Remote Similarity	NPD3206	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD6096	Approved
0.6667	Remote Similarity	NPD6097	Approved
0.6622	Remote Similarity	NPD5368	Approved
0.6613	Remote Similarity	NPD6109	Phase 1
0.6575	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD634	Phase 3
0.6533	Remote Similarity	NPD5369	Approved
0.6447	Remote Similarity	NPD6435	Approved
0.6447	Remote Similarity	NPD4269	Approved
0.6447	Remote Similarity	NPD4270	Approved
0.6418	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4252	Approved
0.6389	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD5362	Discontinued
0.6351	Remote Similarity	NPD4268	Approved
0.6351	Remote Similarity	NPD4271	Approved
0.6269	Remote Similarity	NPD7341	Phase 2
0.6207	Remote Similarity	NPD4220	Pre-registration
0.6203	Remote Similarity	NPD5363	Approved
0.6184	Remote Similarity	NPD4822	Approved
0.6184	Remote Similarity	NPD4819	Approved
0.6184	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4821	Approved
0.6184	Remote Similarity	NPD4820	Approved
0.6176	Remote Similarity	NPD3704	Approved
0.6167	Remote Similarity	NPD3186	Phase 1
0.6125	Remote Similarity	NPD5786	Approved
0.6104	Remote Similarity	NPD857	Phase 3
0.6071	Remote Similarity	NPD2699	Approved
0.6	Remote Similarity	NPD6927	Phase 3
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD3728	Approved
0.5968	Remote Similarity	NPD3730	Approved
0.5968	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD9431	Approved
0.5965	Remote Similarity	NPD9430	Approved
0.5949	Remote Similarity	NPD5331	Approved
0.5949	Remote Similarity	NPD5332	Approved
0.5904	Remote Similarity	NPD6101	Approved
0.5904	Remote Similarity	NPD5347	Phase 2
0.5904	Remote Similarity	NPD5346	Phase 2
0.5904	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD226	Approved
0.5897	Remote Similarity	NPD4790	Discontinued
0.5873	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4793	Discontinued
0.5833	Remote Similarity	NPD5785	Approved
0.5821	Remote Similarity	NPD4193	Approved
0.5821	Remote Similarity	NPD4191	Approved
0.5821	Remote Similarity	NPD4192	Approved
0.5821	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD4695	Discontinued
0.5765	Remote Similarity	NPD6411	Approved
0.5765	Remote Similarity	NPD5281	Approved
0.5765	Remote Similarity	NPD5284	Approved
0.5765	Remote Similarity	NPD7983	Approved
0.575	Remote Similarity	NPD9491	Approved
0.5741	Remote Similarity	NPD77	Approved
0.5741	Remote Similarity	NPD9450	Approved
0.5741	Remote Similarity	NPD5783	Phase 3
0.5732	Remote Similarity	NPD6422	Discontinued
0.5732	Remote Similarity	NPD4249	Approved
0.5714	Remote Similarity	NPD800	Approved
0.5714	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5370	Suspended
0.5698	Remote Similarity	NPD5779	Approved
0.5698	Remote Similarity	NPD5778	Approved
0.569	Remote Similarity	NPD4265	Approved
0.5663	Remote Similarity	NPD4250	Approved
0.5663	Remote Similarity	NPD4251	Approved
0.5647	Remote Similarity	NPD1086	Approved
0.5647	Remote Similarity	NPD6698	Approved
0.5647	Remote Similarity	NPD46	Approved
0.5647	Remote Similarity	NPD1089	Approved
0.5647	Remote Similarity	NPD1090	Approved
0.5632	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4221	Approved
0.5625	Remote Similarity	NPD4223	Phase 3
0.5625	Remote Similarity	NPD3667	Approved
0.5614	Remote Similarity	NPD9411	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