NPASS Compound

Structure

CID76286 OpenBabel06191715412D 33 38 0 0 1 0 0 0 0 0999 V2000 0.5055 -2.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2733 -2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 -3.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1656 -3.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9706 -0.9984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6970 -2.2999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6873 -3.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2095 -3.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2095 -0.5478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4928 -1.8661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7317 -1.4266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4484 -2.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4484 -0.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0061 -1.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 -1.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -1.5331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8565 -1.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1028 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9706 -2.7449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2095 -1.4266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2007 -1.0947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4928 -2.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8568 -0.1957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4476 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7317 -3.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9706 -1.8661 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4484 -1.8661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6873 -1.4266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2379 -0.9876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6873 -0.5478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2443 -3.1788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3794 0.4593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 1 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 21 29 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 23 33 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 30 1 6 0 0 0 29 16 1 6 0 0 0 30 13 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.33
Volume:	494.559
LogP:	5.735
LogD:	4.673
LogS:	-6.085
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	6.24
Fsp3:	0.867
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:	-5.319
MDCK Permeability:	1.6667754607624374e-05
Pgp-inhibitor:	0.79
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.168
20% Bioavailability (F20%):	0.841
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	89.78852081298828%
Volume Distribution (VD):	0.974
Pgp-substrate:	5.406938076019287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.671
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.259
CYP2C9-substrate:	0.286
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	12.714
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.749
Skin Sensitization:	0.043
Carcinogencity:	0.265
Eye Corrosion:	0.007
Eye Irritation:	0.03
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC76286

Natural Product ID:	NPC76286
*Common Name:**	Melliferone
IUPAC Name:	n.a.
Synonyms:	melliferone
Standard InCHIKey:	BHVMSBIGWPPGBF-LHAYROSJSA-N
Standard InCHI:	InChI=1S/C30H44O3/c1-24(2)14-16-29-17-15-28(7)27(6)12-8-19-25(3,4)22(31)10-11-26(19,5)20(27)9-13-30(28,21(29)18-24)33-23(29)32/h9,13,19-21H,8,10-12,14-18H2,1-7H3/t19-,20+,21+,26-,27+,28-,29-,30-/m0/s1
SMILES:	CC1(C)CC[C@]23CC[C@@]4(C)[C@]5(C)CC[C@H]6C(C)(C)C(=O)CC[C@]6(C)[C@H]5C=C[C@@]4([C@@H]2C1)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457498
PubChem CID:	489940
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	0.205	ug.mL-1	PMID[487407]

☑ 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 NPC76286 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	243
0.1-0.2	1541
0.2-0.3	5481
0.3-0.4	15449
0.4-0.5	7701
0.5-0.6	6164
0.6-0.7	5122
0.7-0.8	963
0.8-0.85	26
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9121	High Similarity	NPC10057
0.9022	High Similarity	NPC124703
0.9022	High Similarity	NPC234617
0.8864	High Similarity	NPC474845
0.883	High Similarity	NPC235142
0.8556	High Similarity	NPC173042
0.8384	Intermediate Similarity	NPC301666
0.8372	Intermediate Similarity	NPC267517
0.837	Intermediate Similarity	NPC49420
0.8315	Intermediate Similarity	NPC137493
0.828	Intermediate Similarity	NPC49776
0.828	Intermediate Similarity	NPC63118
0.828	Intermediate Similarity	NPC169343
0.828	Intermediate Similarity	NPC474436
0.8261	Intermediate Similarity	NPC198818
0.8242	Intermediate Similarity	NPC477128
0.8222	Intermediate Similarity	NPC329943
0.8222	Intermediate Similarity	NPC91525
0.8222	Intermediate Similarity	NPC9892
0.8222	Intermediate Similarity	NPC10005
0.8202	Intermediate Similarity	NPC312660
0.8191	Intermediate Similarity	NPC91010
0.8152	Intermediate Similarity	NPC285982
0.8132	Intermediate Similarity	NPC46912
0.8132	Intermediate Similarity	NPC162107
0.8132	Intermediate Similarity	NPC171722
0.8105	Intermediate Similarity	NPC290481
0.8068	Intermediate Similarity	NPC162632
0.8068	Intermediate Similarity	NPC274050
0.8068	Intermediate Similarity	NPC263272
0.8068	Intermediate Similarity	NPC267691
0.8065	Intermediate Similarity	NPC8062
0.8061	Intermediate Similarity	NPC93744
0.8061	Intermediate Similarity	NPC476888
0.8043	Intermediate Similarity	NPC224145
0.8043	Intermediate Similarity	NPC215831
0.798	Intermediate Similarity	NPC40918
0.798	Intermediate Similarity	NPC476890
0.7978	Intermediate Similarity	NPC69101
0.7978	Intermediate Similarity	NPC251779
0.7978	Intermediate Similarity	NPC163236
0.7957	Intermediate Similarity	NPC73995
0.7957	Intermediate Similarity	NPC475049
0.7955	Intermediate Similarity	NPC195424
0.7935	Intermediate Similarity	NPC477228
0.7935	Intermediate Similarity	NPC30421
0.7912	Intermediate Similarity	NPC177932
0.7912	Intermediate Similarity	NPC470223
0.7907	Intermediate Similarity	NPC198473
0.79	Intermediate Similarity	NPC476889
0.79	Intermediate Similarity	NPC254202
0.7895	Intermediate Similarity	NPC118490
0.7889	Intermediate Similarity	NPC70834
0.7872	Intermediate Similarity	NPC159748
0.7872	Intermediate Similarity	NPC193750
0.7872	Intermediate Similarity	NPC101651
0.7872	Intermediate Similarity	NPC474728
0.7872	Intermediate Similarity	NPC120840
0.7872	Intermediate Similarity	NPC291028
0.7872	Intermediate Similarity	NPC113989
0.7865	Intermediate Similarity	NPC20096
0.7865	Intermediate Similarity	NPC474955
0.7865	Intermediate Similarity	NPC48673
0.7857	Intermediate Similarity	NPC164349
0.7849	Intermediate Similarity	NPC40552
0.7849	Intermediate Similarity	NPC246708
0.7841	Intermediate Similarity	NPC16394
0.7841	Intermediate Similarity	NPC231431
0.7835	Intermediate Similarity	NPC327179
0.7835	Intermediate Similarity	NPC322063
0.7826	Intermediate Similarity	NPC470050
0.7826	Intermediate Similarity	NPC470051
0.7812	Intermediate Similarity	NPC60692
0.7812	Intermediate Similarity	NPC84893
0.7812	Intermediate Similarity	NPC74751
0.7812	Intermediate Similarity	NPC148964
0.7812	Intermediate Similarity	NPC477130
0.7812	Intermediate Similarity	NPC477129
0.7802	Intermediate Similarity	NPC96095
0.7802	Intermediate Similarity	NPC156981
0.7789	Intermediate Similarity	NPC285184
0.7789	Intermediate Similarity	NPC38754
0.7789	Intermediate Similarity	NPC77099
0.7789	Intermediate Similarity	NPC60755
0.7789	Intermediate Similarity	NPC470590
0.7789	Intermediate Similarity	NPC105189
0.7778	Intermediate Similarity	NPC186276
0.7778	Intermediate Similarity	NPC476458
0.7778	Intermediate Similarity	NPC258153
0.7766	Intermediate Similarity	NPC281524
0.7766	Intermediate Similarity	NPC470588
0.7766	Intermediate Similarity	NPC474700
0.7766	Intermediate Similarity	NPC30522
0.7755	Intermediate Similarity	NPC84335
0.7755	Intermediate Similarity	NPC76266
0.7755	Intermediate Similarity	NPC473456
0.7755	Intermediate Similarity	NPC204054
0.7755	Intermediate Similarity	NPC257726
0.7755	Intermediate Similarity	NPC38530
0.7753	Intermediate Similarity	NPC37038
0.7742	Intermediate Similarity	NPC51700
0.7742	Intermediate Similarity	NPC18064
0.7742	Intermediate Similarity	NPC242468
0.7742	Intermediate Similarity	NPC102683
0.7742	Intermediate Similarity	NPC98442
0.7742	Intermediate Similarity	NPC307426
0.7742	Intermediate Similarity	NPC171203
0.7742	Intermediate Similarity	NPC130577
0.7742	Intermediate Similarity	NPC293564
0.7742	Intermediate Similarity	NPC88716
0.7742	Intermediate Similarity	NPC142415
0.7742	Intermediate Similarity	NPC231599
0.7742	Intermediate Similarity	NPC68160
0.7732	Intermediate Similarity	NPC127197
0.7732	Intermediate Similarity	NPC84383
0.7732	Intermediate Similarity	NPC83693
0.7723	Intermediate Similarity	NPC36688
0.7717	Intermediate Similarity	NPC474537
0.7717	Intermediate Similarity	NPC189311
0.7708	Intermediate Similarity	NPC272075
0.7708	Intermediate Similarity	NPC214756
0.7708	Intermediate Similarity	NPC202728
0.7708	Intermediate Similarity	NPC86368
0.7708	Intermediate Similarity	NPC158059
0.7708	Intermediate Similarity	NPC118519
0.7708	Intermediate Similarity	NPC295643
0.7701	Intermediate Similarity	NPC41017
0.7692	Intermediate Similarity	NPC470047
0.7692	Intermediate Similarity	NPC22611
0.7692	Intermediate Similarity	NPC470046
0.7692	Intermediate Similarity	NPC200752
0.7684	Intermediate Similarity	NPC273621
0.7684	Intermediate Similarity	NPC212679
0.7684	Intermediate Similarity	NPC210037
0.7684	Intermediate Similarity	NPC152467
0.7684	Intermediate Similarity	NPC18872
0.7684	Intermediate Similarity	NPC220454
0.7684	Intermediate Similarity	NPC328935
0.7684	Intermediate Similarity	NPC227467
0.7684	Intermediate Similarity	NPC469595
0.7684	Intermediate Similarity	NPC120968
0.7684	Intermediate Similarity	NPC290614
0.7684	Intermediate Similarity	NPC477872
0.7684	Intermediate Similarity	NPC7260
0.7684	Intermediate Similarity	NPC327183
0.7677	Intermediate Similarity	NPC471966
0.7677	Intermediate Similarity	NPC176845
0.7674	Intermediate Similarity	NPC166797
0.767	Intermediate Similarity	NPC110496
0.7667	Intermediate Similarity	NPC195334
0.7667	Intermediate Similarity	NPC142244
0.7667	Intermediate Similarity	NPC290495
0.7667	Intermediate Similarity	NPC475665
0.7667	Intermediate Similarity	NPC471898
0.766	Intermediate Similarity	NPC182797
0.766	Intermediate Similarity	NPC17733
0.766	Intermediate Similarity	NPC473242
0.766	Intermediate Similarity	NPC52169
0.766	Intermediate Similarity	NPC226863
0.766	Intermediate Similarity	NPC24816
0.766	Intermediate Similarity	NPC470629
0.766	Intermediate Similarity	NPC474512
0.766	Intermediate Similarity	NPC28227
0.766	Intermediate Similarity	NPC472302
0.766	Intermediate Similarity	NPC181225
0.766	Intermediate Similarity	NPC290690
0.766	Intermediate Similarity	NPC48107
0.7653	Intermediate Similarity	NPC116457
0.7653	Intermediate Similarity	NPC62516
0.7653	Intermediate Similarity	NPC472362
0.7653	Intermediate Similarity	NPC472363
0.7653	Intermediate Similarity	NPC235053
0.7653	Intermediate Similarity	NPC157113
0.7653	Intermediate Similarity	NPC154526
0.7647	Intermediate Similarity	NPC189616
0.7634	Intermediate Similarity	NPC475862
0.7634	Intermediate Similarity	NPC72638
0.7634	Intermediate Similarity	NPC74363
0.7629	Intermediate Similarity	NPC78580
0.7629	Intermediate Similarity	NPC296164
0.7629	Intermediate Similarity	NPC23621
0.7629	Intermediate Similarity	NPC476415
0.7629	Intermediate Similarity	NPC38830
0.7629	Intermediate Similarity	NPC191412
0.7629	Intermediate Similarity	NPC114159
0.7629	Intermediate Similarity	NPC6818
0.7629	Intermediate Similarity	NPC184006
0.7614	Intermediate Similarity	NPC471897
0.7614	Intermediate Similarity	NPC470557
0.7614	Intermediate Similarity	NPC472300
0.7614	Intermediate Similarity	NPC107039
0.7614	Intermediate Similarity	NPC471899
0.7609	Intermediate Similarity	NPC139566
0.7604	Intermediate Similarity	NPC4036
0.7604	Intermediate Similarity	NPC187722
0.7604	Intermediate Similarity	NPC65120
0.7604	Intermediate Similarity	NPC474525
0.7604	Intermediate Similarity	NPC145067
0.7604	Intermediate Similarity	NPC158030
0.7604	Intermediate Similarity	NPC6255

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 NPC76286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	1609
0.2-0.3	4078
0.3-0.4	2218
0.4-0.5	589
0.5-0.6	204
0.6-0.7	182
0.7-0.8	34
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
0.8	Intermediate Similarity	NPD7900	Approved
0.8	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3573	Approved
0.7912	Intermediate Similarity	NPD1694	Approved
0.7812	Intermediate Similarity	NPD7748	Approved
0.7755	Intermediate Similarity	NPD7902	Approved
0.7732	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6098	Approved
0.7629	Intermediate Similarity	NPD6001	Approved
0.7604	Intermediate Similarity	NPD5693	Phase 1
0.7604	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD5207	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD6673	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.7391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD6903	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7292	Intermediate Similarity	NPD5208	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7172	Intermediate Similarity	NPD6399	Phase 3
0.7157	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD4519	Discontinued
0.7083	Intermediate Similarity	NPD4623	Approved
0.7071	Intermediate Similarity	NPD8034	Phase 2
0.7071	Intermediate Similarity	NPD5694	Approved
0.7071	Intermediate Similarity	NPD6050	Approved
0.7071	Intermediate Similarity	NPD8035	Phase 2
0.7041	Intermediate Similarity	NPD6051	Approved
0.7041	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8039	Approved
0.6979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5692	Phase 3
0.6916	Remote Similarity	NPD6008	Approved
0.6907	Remote Similarity	NPD3618	Phase 1
0.6907	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5281	Approved
0.69	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD6084	Phase 2
0.6893	Remote Similarity	NPD6083	Phase 2
0.6887	Remote Similarity	NPD6052	Approved
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD5696	Approved
0.6804	Remote Similarity	NPD5329	Approved
0.6796	Remote Similarity	NPD7732	Phase 3
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6757	Remote Similarity	NPD6649	Approved
0.6757	Remote Similarity	NPD6650	Approved
0.6733	Remote Similarity	NPD6079	Approved
0.6727	Remote Similarity	NPD6373	Approved
0.6727	Remote Similarity	NPD6372	Approved
0.6702	Remote Similarity	NPD7645	Phase 2
0.6701	Remote Similarity	NPD4786	Approved
0.6701	Remote Similarity	NPD4197	Approved
0.67	Remote Similarity	NPD5328	Approved
0.6699	Remote Similarity	NPD5695	Phase 3
0.6697	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD6614	Approved
0.6697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD7614	Phase 1
0.6635	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4137	Phase 3
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD4689	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6566	Remote Similarity	NPD4688	Approved
0.6556	Remote Similarity	NPD4691	Approved
0.6556	Remote Similarity	NPD4747	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6549	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD5654	Approved
0.6531	Remote Similarity	NPD3133	Approved
0.6531	Remote Similarity	NPD3666	Approved
0.6531	Remote Similarity	NPD3668	Phase 3
0.6531	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD4058	Approved
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4202	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5777	Approved
0.6481	Remote Similarity	NPD7632	Discontinued
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3617	Approved
0.6415	Remote Similarity	NPD5959	Approved
0.6408	Remote Similarity	NPD6411	Approved
0.64	Remote Similarity	NPD4694	Approved
0.64	Remote Similarity	NPD5280	Approved
0.6381	Remote Similarity	NPD4629	Approved
0.6381	Remote Similarity	NPD5210	Approved
0.6373	Remote Similarity	NPD4753	Phase 2
0.6354	Remote Similarity	NPD4195	Approved
0.6348	Remote Similarity	NPD7094	Approved
0.6348	Remote Similarity	NPD6858	Approved
0.6344	Remote Similarity	NPD4687	Approved
0.6344	Remote Similarity	NPD5733	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.633	Remote Similarity	NPD5211	Phase 2
0.6321	Remote Similarity	NPD5221	Approved
0.6321	Remote Similarity	NPD4697	Phase 3
0.6321	Remote Similarity	NPD5222	Approved
0.6321	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7507	Approved
0.6311	Remote Similarity	NPD5785	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6292	Remote Similarity	NPD4224	Phase 2
0.6283	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8328	Phase 3
0.6271	Remote Similarity	NPD6335	Approved
0.6263	Remote Similarity	NPD4788	Approved
0.6262	Remote Similarity	NPD5173	Approved
0.6262	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.6224	Remote Similarity	NPD4692	Approved
0.6224	Remote Similarity	NPD4139	Approved
0.6224	Remote Similarity	NPD8028	Phase 2
0.6218	Remote Similarity	NPD7100	Approved
0.6218	Remote Similarity	NPD7101	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6214	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6101	Approved
0.621	Remote Similarity	NPD7736	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.6207	Remote Similarity	NPD8133	Approved
0.619	Remote Similarity	NPD5778	Approved
0.619	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD6317	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.617	Remote Similarity	NPD4785	Approved
0.617	Remote Similarity	NPD4784	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6154	Remote Similarity	NPD5360	Phase 3
0.6154	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4700	Approved
0.6147	Remote Similarity	NPD6404	Discontinued
0.6134	Remote Similarity	NPD6314	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6129	Remote Similarity	NPD4243	Approved
0.6129	Remote Similarity	NPD6081	Approved
0.6129	Remote Similarity	NPD5276	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD7525	Registered
0.6116	Remote Similarity	NPD8517	Approved
0.6116	Remote Similarity	NPD8513	Phase 3
0.6116	Remote Similarity	NPD8515	Approved
0.6116	Remote Similarity	NPD8516	Approved
0.6116	Remote Similarity	NPD7503	Approved
0.6106	Remote Similarity	NPD6412	Phase 2
0.6102	Remote Similarity	NPD6274	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6078	Remote Similarity	NPD5279	Phase 3
0.6075	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5369	Approved
0.605	Remote Similarity	NPD6009	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