NPASS Compound

Structure

CID151719 OpenBabel06191715522D 23 22 0 0 0 0 0 0 0 0999 V2000 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.36
Volume:	403.728
LogP:	9.911
LogD:	5.15
LogS:	-4.812
# Rotatable Bonds:	19
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	1.69
Fsp3:	0.913
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032
MDCK Permeability:	1.0218452189292293e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.659
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	100.05001068115234%
Volume Distribution (VD):	5.206
Pgp-substrate:	0.8668328523635864%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.206
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.321
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	4.053
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.591
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.973
Carcinogencity:	0.029
Eye Corrosion:	0.99
Eye Irritation:	0.967
Respiratory Toxicity:	0.425

Download Data

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

Natural Product: NPC151719

Natural Product ID:	NPC151719
*Common Name:**	(Z)-Tricos-9-Ene
IUPAC Name:	(Z)-tricos-9-ene
Synonyms:
Standard InCHIKey:	IGOWHGRNPLFNDJ-ZPHPHTNESA-N
Standard InCHI:	InChI=1S/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17-
SMILES:	CCCCCCCC/C=CCCCCCCCCCCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1894305
PubChem CID:	5365075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002837] Hydrocarbons [CHEMONTID:0004475] Unsaturated hydrocarbons [CHEMONTID:0004476] Unsaturated aliphatic hydrocarbons

*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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8714	Elaeocarpus mastersii	Species	Elaeocarpaceae	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
Potency	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[478581]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	1.0	nM	PMID[478581]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	1.4	nM	PMID[478581]

☑ 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 NPC151719 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	671
0.1-0.2	25157
0.2-0.3	12519
0.3-0.4	3212
0.4-0.5	741
0.5-0.6	314
0.6-0.7	56
0.7-0.8	13
0.8-0.85	7
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC34671
0.9062	High Similarity	NPC182392
0.8966	High Similarity	NPC76765
0.8966	High Similarity	NPC179103
0.8966	High Similarity	NPC138325
0.871	High Similarity	NPC471327
0.8276	Intermediate Similarity	NPC266144
0.8276	Intermediate Similarity	NPC266539
0.8276	Intermediate Similarity	NPC287191
0.8276	Intermediate Similarity	NPC31891
0.8182	Intermediate Similarity	NPC62779
0.8065	Intermediate Similarity	NPC115959
0.8065	Intermediate Similarity	NPC123965
0.7931	Intermediate Similarity	NPC38513
0.7931	Intermediate Similarity	NPC88325
0.7714	Intermediate Similarity	NPC92224
0.7647	Intermediate Similarity	NPC173592
0.7647	Intermediate Similarity	NPC305759
0.7647	Intermediate Similarity	NPC99088
0.7576	Intermediate Similarity	NPC3649
0.7576	Intermediate Similarity	NPC196831
0.7576	Intermediate Similarity	NPC100879
0.75	Intermediate Similarity	NPC138113
0.7297	Intermediate Similarity	NPC266298
0.7273	Intermediate Similarity	NPC60288
0.7059	Intermediate Similarity	NPC206088
0.7059	Intermediate Similarity	NPC66577
0.6905	Remote Similarity	NPC76976
0.6842	Remote Similarity	NPC139717
0.6842	Remote Similarity	NPC297643
0.6842	Remote Similarity	NPC229262
0.6765	Remote Similarity	NPC16561
0.6757	Remote Similarity	NPC282119
0.6744	Remote Similarity	NPC163751
0.6744	Remote Similarity	NPC110234
0.6744	Remote Similarity	NPC323445
0.6744	Remote Similarity	NPC44363
0.6667	Remote Similarity	NPC217923
0.6667	Remote Similarity	NPC267514
0.6667	Remote Similarity	NPC108195
0.6667	Remote Similarity	NPC64176
0.6667	Remote Similarity	NPC288991
0.6667	Remote Similarity	NPC262789
0.6667	Remote Similarity	NPC145755
0.6591	Remote Similarity	NPC124851
0.6585	Remote Similarity	NPC298710
0.6585	Remote Similarity	NPC149668
0.6585	Remote Similarity	NPC67920
0.6585	Remote Similarity	NPC287397
0.6585	Remote Similarity	NPC177470
0.6579	Remote Similarity	NPC190810
0.6579	Remote Similarity	NPC76145
0.6579	Remote Similarity	NPC34764
0.6552	Remote Similarity	NPC178306
0.6512	Remote Similarity	NPC239754
0.6512	Remote Similarity	NPC269074
0.6512	Remote Similarity	NPC49088
0.65	Remote Similarity	NPC183670
0.6444	Remote Similarity	NPC17810
0.6444	Remote Similarity	NPC98284
0.6429	Remote Similarity	NPC252978
0.641	Remote Similarity	NPC155880
0.641	Remote Similarity	NPC239039
0.641	Remote Similarity	NPC92863
0.6389	Remote Similarity	NPC213749
0.6364	Remote Similarity	NPC55063
0.6364	Remote Similarity	NPC19834
0.6341	Remote Similarity	NPC218918
0.6341	Remote Similarity	NPC33489
0.6341	Remote Similarity	NPC120926
0.6341	Remote Similarity	NPC144023
0.6304	Remote Similarity	NPC473913
0.6304	Remote Similarity	NPC59051
0.6304	Remote Similarity	NPC249670
0.6304	Remote Similarity	NPC474642
0.625	Remote Similarity	NPC15934
0.6222	Remote Similarity	NPC471958
0.6207	Remote Similarity	NPC225855
0.619	Remote Similarity	NPC473912
0.617	Remote Similarity	NPC262968
0.617	Remote Similarity	NPC477458
0.617	Remote Similarity	NPC261571
0.6136	Remote Similarity	NPC276825
0.6098	Remote Similarity	NPC329762
0.6098	Remote Similarity	NPC103236
0.6098	Remote Similarity	NPC27444
0.6087	Remote Similarity	NPC248884
0.6087	Remote Similarity	NPC22765
0.6087	Remote Similarity	NPC31194
0.6087	Remote Similarity	NPC17518
0.6087	Remote Similarity	NPC85079
0.6087	Remote Similarity	NPC207815
0.6047	Remote Similarity	NPC86538
0.6047	Remote Similarity	NPC60556
0.6047	Remote Similarity	NPC109813
0.6042	Remote Similarity	NPC188341
0.6042	Remote Similarity	NPC49494
0.6042	Remote Similarity	NPC92114
0.6	Remote Similarity	NPC180575
0.6	Remote Similarity	NPC40434
0.6	Remote Similarity	NPC34873
0.6	Remote Similarity	NPC45727
0.6	Remote Similarity	NPC100380
0.6	Remote Similarity	NPC180840
0.6	Remote Similarity	NPC48638
0.5957	Remote Similarity	NPC471281
0.5957	Remote Similarity	NPC199286
0.5957	Remote Similarity	NPC224227
0.5957	Remote Similarity	NPC477727
0.5957	Remote Similarity	NPC26960
0.5957	Remote Similarity	NPC182102
0.5957	Remote Similarity	NPC72699
0.5952	Remote Similarity	NPC270170
0.5952	Remote Similarity	NPC269823
0.5952	Remote Similarity	NPC7754
0.5946	Remote Similarity	NPC13217
0.5918	Remote Similarity	NPC39633
0.5918	Remote Similarity	NPC139545
0.5918	Remote Similarity	NPC309606
0.5909	Remote Similarity	NPC138935
0.5909	Remote Similarity	NPC248411
0.5909	Remote Similarity	NPC101616
0.5909	Remote Similarity	NPC202189
0.587	Remote Similarity	NPC91495
0.587	Remote Similarity	NPC178644
0.5862	Remote Similarity	NPC33192
0.5862	Remote Similarity	NPC26229
0.5862	Remote Similarity	NPC77249
0.5862	Remote Similarity	NPC154477
0.5862	Remote Similarity	NPC239406
0.5862	Remote Similarity	NPC26974
0.5854	Remote Similarity	NPC33761
0.5833	Remote Similarity	NPC473672
0.5833	Remote Similarity	NPC256656
0.5833	Remote Similarity	NPC9273
0.5833	Remote Similarity	NPC224148
0.5833	Remote Similarity	NPC234829
0.5833	Remote Similarity	NPC197272
0.5833	Remote Similarity	NPC151782
0.5833	Remote Similarity	NPC477723
0.5833	Remote Similarity	NPC474495
0.5833	Remote Similarity	NPC165447
0.5833	Remote Similarity	NPC475477
0.5833	Remote Similarity	NPC76198
0.5833	Remote Similarity	NPC471959
0.5833	Remote Similarity	NPC89824
0.5833	Remote Similarity	NPC329608
0.5833	Remote Similarity	NPC170776
0.5833	Remote Similarity	NPC294278
0.5833	Remote Similarity	NPC55383
0.5814	Remote Similarity	NPC213538
0.5814	Remote Similarity	NPC256766
0.5814	Remote Similarity	NPC304151
0.5814	Remote Similarity	NPC208936
0.58	Remote Similarity	NPC281972
0.58	Remote Similarity	NPC87564
0.58	Remote Similarity	NPC32467
0.58	Remote Similarity	NPC6095
0.58	Remote Similarity	NPC261831
0.58	Remote Similarity	NPC25417
0.58	Remote Similarity	NPC424
0.58	Remote Similarity	NPC85813
0.58	Remote Similarity	NPC154245
0.58	Remote Similarity	NPC290563
0.58	Remote Similarity	NPC88966
0.5778	Remote Similarity	NPC86683
0.5778	Remote Similarity	NPC474202
0.5778	Remote Similarity	NPC474362
0.5778	Remote Similarity	NPC296337
0.575	Remote Similarity	NPC216416
0.575	Remote Similarity	NPC185839
0.5745	Remote Similarity	NPC471280
0.5745	Remote Similarity	NPC471275
0.5745	Remote Similarity	NPC471276
0.5745	Remote Similarity	NPC153538
0.5745	Remote Similarity	NPC125122
0.5745	Remote Similarity	NPC302310
0.5714	Remote Similarity	NPC208638
0.5686	Remote Similarity	NPC228473
0.5686	Remote Similarity	NPC474644
0.5686	Remote Similarity	NPC200845
0.5686	Remote Similarity	NPC128061
0.5686	Remote Similarity	NPC10316
0.5686	Remote Similarity	NPC470893
0.5686	Remote Similarity	NPC28779
0.5686	Remote Similarity	NPC223677
0.5682	Remote Similarity	NPC301972
0.5682	Remote Similarity	NPC116934
0.5682	Remote Similarity	NPC270796
0.5652	Remote Similarity	NPC262558
0.5652	Remote Similarity	NPC8610
0.5652	Remote Similarity	NPC35141
0.5652	Remote Similarity	NPC124183
0.5625	Remote Similarity	NPC474391
0.5625	Remote Similarity	NPC329773
0.56	Remote Similarity	NPC70387
0.56	Remote Similarity	NPC321062
0.56	Remote Similarity	NPC294548
0.56	Remote Similarity	NPC36061
0.56	Remote Similarity	NPC476679

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 NPC151719 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	715
0.1-0.2	6718
0.2-0.3	1454
0.3-0.4	213
0.4-0.5	29
0.5-0.6	19
0.6-0.7	2
0.7-0.8	0
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
0.6579	Remote Similarity	NPD319	Phase 1
0.6444	Remote Similarity	NPD8262	Approved
0.625	Remote Similarity	NPD5783	Phase 3
0.617	Remote Similarity	NPD29	Approved
0.617	Remote Similarity	NPD28	Approved
0.6136	Remote Similarity	NPD39	Approved
0.58	Remote Similarity	NPD4266	Approved
0.58	Remote Similarity	NPD3194	Approved
0.58	Remote Similarity	NPD3196	Approved
0.58	Remote Similarity	NPD3195	Phase 2
0.5778	Remote Similarity	NPD3174	Discontinued
0.5682	Remote Similarity	NPD5326	Phase 3
0.56	Remote Similarity	NPD3172	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