NPASS Compound

Structure

CID44682 OpenBabel06191715382D 81 86 0 0 1 0 0 0 0 0999 V2000 3.1806 -5.3575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2247 -2.8330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 5.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5364 -1.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 4.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2247 2.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4241 -2.5650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 -0.8835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8481 -1.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2316 -4.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2247 -1.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 4.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4141 -3.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6528 0.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5319 -0.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5920 0.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2410 -0.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3554 1.4939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4652 -2.8798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8087 -1.0782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9662 1.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6477 -2.3490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2773 -1.3148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4624 2.2171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4716 0.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3806 -1.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4374 4.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3806 2.5280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1229 -1.6380 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5932 0.0912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8481 -0.8835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6987 -1.3756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6275 0.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8933 2.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3806 3.5027 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4374 0.5786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5122 -1.2057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6923 -0.3962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6275 1.5533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5364 3.9901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4374 1.5533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3324 -0.6524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6923 3.5027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6923 0.5786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7833 2.0406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5932 2.0406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2366 -0.5314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8481 1.0659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0608 1.5533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3806 0.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4374 3.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6923 2.5280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0040 0.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6259 -0.9638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7491 1.5533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0608 0.5786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9443 3.3115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2247 3.9901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 0.0912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4656 -1.4083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5364 -0.8835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4716 2.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5364 4.9648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 2.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9846 0.0720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8481 3.9901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2247 1.0659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2815 3.0154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1599 1.0659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5364 2.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0040 -0.3962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4461 -1.5170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7491 0.5786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1297 -1.2546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7833 0.0912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3148 2.2773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5364 1.0659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 3.0154 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 5.8481 2.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9049 2.0406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 10 13 1 0 0 0 0 11 26 2 0 0 0 0 12 27 2 0 0 0 0 13 19 1 0 0 0 0 14 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 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 23 32 1 0 0 0 0 24 34 1 0 0 0 0 25 69 1 0 0 0 0 26 50 1 0 0 0 0 27 51 1 0 0 0 0 28 6 1 6 0 0 0 28 35 1 0 0 0 0 28 70 1 0 0 0 0 29 7 1 6 0 0 0 29 37 1 0 0 0 0 29 72 1 0 0 0 0 30 8 1 1 0 0 0 30 36 1 0 0 0 0 30 73 1 0 0 0 0 31 9 1 1 0 0 0 31 38 1 0 0 0 0 31 71 1 0 0 0 0 32 22 1 6 0 0 0 32 74 1 0 0 0 0 33 25 1 1 0 0 0 33 39 1 0 0 0 0 33 75 1 0 0 0 0 34 57 2 0 0 0 0 34 76 1 0 0 0 0 35 40 1 0 0 0 0 35 58 1 1 0 0 0 36 41 1 0 0 0 0 36 59 1 6 0 0 0 37 42 1 0 0 0 0 37 60 1 1 0 0 0 38 44 1 0 0 0 0 38 61 1 6 0 0 0 39 45 1 0 0 0 0 39 62 1 6 0 0 0 40 43 1 0 0 0 0 40 63 1 6 0 0 0 41 46 1 0 0 0 0 41 64 1 1 0 0 0 42 47 1 0 0 0 0 42 65 1 6 0 0 0 43 52 1 0 0 0 0 43 66 1 6 0 0 0 44 48 1 0 0 0 0 44 77 1 1 0 0 0 45 49 1 0 0 0 0 45 76 1 1 0 0 0 46 55 1 0 0 0 0 46 78 1 1 0 0 0 47 54 1 0 0 0 0 47 79 1 1 0 0 0 48 53 1 0 0 0 0 48 80 1 6 0 0 0 49 56 1 0 0 0 0 49 81 1 6 0 0 0 50 67 2 0 0 0 0 50 77 1 0 0 0 0 51 68 2 0 0 0 0 51 78 1 0 0 0 0 52 70 1 0 0 0 0 52 80 1 1 0 0 0 53 69 1 1 0 0 0 53 71 1 0 0 0 0 54 72 1 6 0 0 0 54 74 1 0 0 0 0 55 73 1 0 0 0 0 55 81 1 6 0 0 0 56 75 1 6 0 0 0 56 79 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1164.59
Volume:	1132.366
LogP:	4.215
LogD:	2.335
LogS:	-3.464
# Rotatable Bonds:	17
TPSA:	353.27
# H-Bond Aceptor:	25
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.048
Synthetic Accessibility Score:	2.87
Fsp3:	0.875
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.657
MDCK Permeability:	0.0004157626535743475
Pgp-inhibitor:	0.523
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.878
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	85.72551727294922%
Volume Distribution (VD):	0.327
Pgp-substrate:	11.843584060668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	0.554
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.968
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.922
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.205

Download Data

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

Natural Product: NPC44682

Natural Product ID:	NPC44682
*Common Name:**	Albinoside Iii
IUPAC Name:	n.a.
Synonyms:	Albinoside III
Standard InCHIKey:	HUCKMCHVBAWQIA-DGBHNKMOSA-N
Standard InCHI:	InChI=1S/C56H92O25/c1-10-13-19-22-32-23-20-17-15-14-16-18-21-24-34(57)76-45-39(62)33(25-69-53-48(80-52-43(66)40(63)35(58)28(6)70-52)44(38(61)31(9)71-53)77-50(67)26(4)11-2)75-56(79-47-42(65)37(60)29(7)72-54(47)74-32)49(45)81-55-46(78-51(68)27(5)12-3)41(64)36(59)30(8)73-55/h11-12,28-33,35-49,52-56,58-66H,10,13-25H2,1-9H3/b26-11+,27-12+/t28-,29+,30-,31+,32-,33+,35-,36-,37+,38+,39+,40+,41+,42-,43+,44-,45-,46+,47+,48+,49+,52-,53+,54-,55-,56-/m0/s1
SMILES:	CCCCC[C@H]1CCCCCCCCCC(=O)O[C@H]2[C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)OC(=O)/C(=C/C)/C)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O[C@H]([C@@H]2O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)OC(=O)/C(=C/C)/C)O[C@@H]2[C@H]([C@@H]([C@@H](C)O[C@H]2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146620
PubChem CID:	71451029
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22924480]
NPO13214	Ipomoea alba	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28006904]
NPO13214	Ipomoea alba	Species	Convolvulaceae	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	3

Activity Type	# Activity
Cell Line	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[522248]
NPT2	Others	Unspecified		FC	>	1687.5	n.a.	PMID[522248]
NPT2	Others	Unspecified		FC	>	2140.6	n.a.	PMID[522248]
NPT2	Others	Unspecified		FC	>	73.4	n.a.	PMID[522248]

☑ 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 NPC44682 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	298
0.1-0.2	2505
0.2-0.3	7281
0.3-0.4	14593
0.4-0.5	10053
0.5-0.6	5373
0.6-0.7	1817
0.7-0.8	707
0.8-0.85	49
0.85-0.9	0
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC163409
0.977	High Similarity	NPC477349
0.9551	High Similarity	NPC477345
0.9551	High Similarity	NPC477348
0.9551	High Similarity	NPC238264
0.9341	High Similarity	NPC475375
0.9341	High Similarity	NPC473605
0.9341	High Similarity	NPC475525
0.9341	High Similarity	NPC476066
0.9341	High Similarity	NPC475164
0.9341	High Similarity	NPC475241
0.9341	High Similarity	NPC475540
0.9341	High Similarity	NPC475593
0.9341	High Similarity	NPC473765
0.8539	High Similarity	NPC288471
0.8298	Intermediate Similarity	NPC110072
0.8295	Intermediate Similarity	NPC267592
0.8276	Intermediate Similarity	NPC477325
0.8276	Intermediate Similarity	NPC477323
0.8276	Intermediate Similarity	NPC475425
0.8276	Intermediate Similarity	NPC109887
0.8276	Intermediate Similarity	NPC477330
0.8276	Intermediate Similarity	NPC477320
0.8276	Intermediate Similarity	NPC113745
0.8276	Intermediate Similarity	NPC281563
0.8276	Intermediate Similarity	NPC477329
0.8276	Intermediate Similarity	NPC477328
0.8276	Intermediate Similarity	NPC477326
0.8276	Intermediate Similarity	NPC146380
0.8202	Intermediate Similarity	NPC477319
0.8202	Intermediate Similarity	NPC184915
0.8202	Intermediate Similarity	NPC169345
0.8202	Intermediate Similarity	NPC472200
0.8202	Intermediate Similarity	NPC472202
0.8202	Intermediate Similarity	NPC224953
0.8202	Intermediate Similarity	NPC472204
0.8202	Intermediate Similarity	NPC123204
0.8202	Intermediate Similarity	NPC472201
0.8202	Intermediate Similarity	NPC183888
0.8202	Intermediate Similarity	NPC477331
0.8202	Intermediate Similarity	NPC477318
0.8202	Intermediate Similarity	NPC472203
0.8202	Intermediate Similarity	NPC143421
0.8202	Intermediate Similarity	NPC89843
0.8202	Intermediate Similarity	NPC307400
0.8202	Intermediate Similarity	NPC27289
0.8202	Intermediate Similarity	NPC126685
0.8202	Intermediate Similarity	NPC44782
0.8202	Intermediate Similarity	NPC119583
0.8202	Intermediate Similarity	NPC472205
0.8202	Intermediate Similarity	NPC259294
0.8202	Intermediate Similarity	NPC290012
0.8202	Intermediate Similarity	NPC477317
0.8202	Intermediate Similarity	NPC115013
0.8085	Intermediate Similarity	NPC285588
0.8046	Intermediate Similarity	NPC477350
0.8022	Intermediate Similarity	NPC477332
0.8022	Intermediate Similarity	NPC60849
0.8022	Intermediate Similarity	NPC472352
0.7978	Intermediate Similarity	NPC146992
0.7978	Intermediate Similarity	NPC294748
0.7978	Intermediate Similarity	NPC22742
0.7978	Intermediate Similarity	NPC85759
0.7978	Intermediate Similarity	NPC477344
0.7978	Intermediate Similarity	NPC477346
0.7978	Intermediate Similarity	NPC158302
0.7955	Intermediate Similarity	NPC476783
0.7955	Intermediate Similarity	NPC476781
0.7955	Intermediate Similarity	NPC216883
0.7955	Intermediate Similarity	NPC476782
0.7864	Intermediate Similarity	NPC315070
0.7835	Intermediate Similarity	NPC320089
0.7822	Intermediate Similarity	NPC154132
0.7822	Intermediate Similarity	NPC57586
0.7822	Intermediate Similarity	NPC2313
0.7822	Intermediate Similarity	NPC475655
0.7822	Intermediate Similarity	NPC475157
0.7822	Intermediate Similarity	NPC471637
0.7802	Intermediate Similarity	NPC476087
0.7802	Intermediate Similarity	NPC475270
0.7802	Intermediate Similarity	NPC475667
0.7802	Intermediate Similarity	NPC475327
0.7802	Intermediate Similarity	NPC238056
0.7802	Intermediate Similarity	NPC297768
0.7802	Intermediate Similarity	NPC186992
0.7802	Intermediate Similarity	NPC269318
0.7802	Intermediate Similarity	NPC173328
0.7802	Intermediate Similarity	NPC477347
0.7701	Intermediate Similarity	NPC9763
0.7701	Intermediate Similarity	NPC39266
0.7701	Intermediate Similarity	NPC225748
0.7701	Intermediate Similarity	NPC169085
0.7701	Intermediate Similarity	NPC206823
0.7701	Intermediate Similarity	NPC163812
0.7684	Intermediate Similarity	NPC475186
0.7684	Intermediate Similarity	NPC118077
0.7634	Intermediate Similarity	NPC38295
0.7634	Intermediate Similarity	NPC470313
0.7634	Intermediate Similarity	NPC156089
0.7634	Intermediate Similarity	NPC473500
0.76	Intermediate Similarity	NPC143446
0.7576	Intermediate Similarity	NPC159698
0.7565	Intermediate Similarity	NPC297950
0.7547	Intermediate Similarity	NPC193765
0.7524	Intermediate Similarity	NPC476738
0.7524	Intermediate Similarity	NPC476740
0.75	Intermediate Similarity	NPC474581
0.75	Intermediate Similarity	NPC469543
0.75	Intermediate Similarity	NPC309398
0.75	Intermediate Similarity	NPC127295
0.75	Intermediate Similarity	NPC163362
0.75	Intermediate Similarity	NPC125142
0.75	Intermediate Similarity	NPC297945
0.75	Intermediate Similarity	NPC126897
0.75	Intermediate Similarity	NPC473816
0.75	Intermediate Similarity	NPC475367
0.75	Intermediate Similarity	NPC197736
0.7475	Intermediate Similarity	NPC472195
0.7475	Intermediate Similarity	NPC238090
0.7475	Intermediate Similarity	NPC472196
0.7471	Intermediate Similarity	NPC52268
0.7471	Intermediate Similarity	NPC53760
0.7436	Intermediate Similarity	NPC23020
0.7436	Intermediate Similarity	NPC220838
0.7436	Intermediate Similarity	NPC472268
0.7436	Intermediate Similarity	NPC472269
0.7436	Intermediate Similarity	NPC472270
0.7436	Intermediate Similarity	NPC112492
0.7436	Intermediate Similarity	NPC45606
0.7434	Intermediate Similarity	NPC476150
0.7434	Intermediate Similarity	NPC476127
0.7419	Intermediate Similarity	NPC469469
0.7419	Intermediate Similarity	NPC21693
0.7419	Intermediate Similarity	NPC236649
0.74	Intermediate Similarity	NPC294293
0.7396	Intermediate Similarity	NPC47937
0.7383	Intermediate Similarity	NPC177524
0.7383	Intermediate Similarity	NPC392
0.7383	Intermediate Similarity	NPC219900
0.7373	Intermediate Similarity	NPC28069
0.7373	Intermediate Similarity	NPC77651
0.7356	Intermediate Similarity	NPC211428
0.7356	Intermediate Similarity	NPC241265
0.7356	Intermediate Similarity	NPC285003
0.735	Intermediate Similarity	NPC470516
0.7345	Intermediate Similarity	NPC470915
0.7345	Intermediate Similarity	NPC470911
0.7345	Intermediate Similarity	NPC470517
0.7311	Intermediate Similarity	NPC290276
0.7311	Intermediate Similarity	NPC300655
0.7311	Intermediate Similarity	NPC198918
0.7311	Intermediate Similarity	NPC204214
0.7311	Intermediate Similarity	NPC124878
0.7311	Intermediate Similarity	NPC92283
0.7311	Intermediate Similarity	NPC147032
0.7311	Intermediate Similarity	NPC10121
0.7311	Intermediate Similarity	NPC222951
0.7311	Intermediate Similarity	NPC10883
0.7311	Intermediate Similarity	NPC43589
0.7311	Intermediate Similarity	NPC231888
0.7311	Intermediate Similarity	NPC35338
0.7311	Intermediate Similarity	NPC63404
0.7311	Intermediate Similarity	NPC311178
0.7308	Intermediate Similarity	NPC476611
0.73	Intermediate Similarity	NPC475173
0.73	Intermediate Similarity	NPC473663
0.73	Intermediate Similarity	NPC473561
0.73	Intermediate Similarity	NPC473520
0.73	Intermediate Similarity	NPC473723
0.7292	Intermediate Similarity	NPC329615
0.7292	Intermediate Similarity	NPC471567
0.7292	Intermediate Similarity	NPC182383
0.7292	Intermediate Similarity	NPC477013
0.7292	Intermediate Similarity	NPC470124
0.7292	Intermediate Similarity	NPC120398
0.7292	Intermediate Similarity	NPC477014
0.7292	Intermediate Similarity	NPC329838
0.7288	Intermediate Similarity	NPC162925
0.7288	Intermediate Similarity	NPC87153
0.7273	Intermediate Similarity	NPC473311
0.7273	Intermediate Similarity	NPC473904
0.7264	Intermediate Similarity	NPC231271
0.7264	Intermediate Similarity	NPC470519
0.7257	Intermediate Similarity	NPC471548
0.7257	Intermediate Similarity	NPC470515
0.7255	Intermediate Similarity	NPC306041
0.725	Intermediate Similarity	NPC319719
0.725	Intermediate Similarity	NPC233223
0.725	Intermediate Similarity	NPC322904
0.725	Intermediate Similarity	NPC324933
0.725	Intermediate Similarity	NPC196874
0.725	Intermediate Similarity	NPC471025
0.725	Intermediate Similarity	NPC475444
0.725	Intermediate Similarity	NPC183816
0.725	Intermediate Similarity	NPC475177
0.725	Intermediate Similarity	NPC473679
0.7245	Intermediate Similarity	NPC89001
0.7245	Intermediate Similarity	NPC473905
0.7245	Intermediate Similarity	NPC40376
0.7245	Intermediate Similarity	NPC320458

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 NPC44682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	2857
0.2-0.3	3886
0.3-0.4	1423
0.4-0.5	511
0.5-0.6	122
0.6-0.7	25
0.7-0.8	8
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
0.75	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6686	Approved
0.71	Intermediate Similarity	NPD6698	Approved
0.71	Intermediate Similarity	NPD46	Approved
0.7069	Intermediate Similarity	NPD8516	Approved
0.7069	Intermediate Similarity	NPD8515	Approved
0.7069	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD8133	Approved
0.6952	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8513	Phase 3
0.6842	Remote Similarity	NPD7329	Approved
0.6555	Remote Similarity	NPD8377	Approved
0.6555	Remote Similarity	NPD8294	Approved
0.6529	Remote Similarity	NPD8328	Phase 3
0.6529	Remote Similarity	NPD7830	Approved
0.6529	Remote Similarity	NPD7829	Approved
0.65	Remote Similarity	NPD8378	Approved
0.65	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD8296	Approved
0.65	Remote Similarity	NPD8380	Approved
0.65	Remote Similarity	NPD8335	Approved
0.6442	Remote Similarity	NPD7838	Discovery
0.6437	Remote Similarity	NPD6123	Approved
0.6423	Remote Similarity	NPD7507	Approved
0.6372	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD8033	Approved
0.627	Remote Similarity	NPD7319	Approved
0.6261	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7503	Approved
0.6226	Remote Similarity	NPD7983	Approved
0.6116	Remote Similarity	NPD7328	Approved
0.6116	Remote Similarity	NPD7327	Approved
0.6111	Remote Similarity	NPD8448	Approved
0.6098	Remote Similarity	NPD8444	Approved
0.6094	Remote Similarity	NPD8391	Approved
0.6094	Remote Similarity	NPD8392	Approved
0.6094	Remote Similarity	NPD8390	Approved
0.6087	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7516	Approved
0.6042	Remote Similarity	NPD3181	Approved
0.6033	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5984	Remote Similarity	NPD7641	Discontinued
0.5984	Remote Similarity	NPD8074	Phase 3
0.5913	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7839	Suspended
0.5851	Remote Similarity	NPD898	Approved
0.5851	Remote Similarity	NPD896	Approved
0.5851	Remote Similarity	NPD897	Approved
0.5827	Remote Similarity	NPD8341	Approved
0.5827	Remote Similarity	NPD8299	Approved
0.5827	Remote Similarity	NPD8340	Approved
0.5827	Remote Similarity	NPD8342	Approved
0.5798	Remote Similarity	NPD6371	Approved
0.5747	Remote Similarity	NPD3728	Approved
0.5747	Remote Similarity	NPD3730	Approved
0.5747	Remote Similarity	NPD7346	Approved
0.5739	Remote Similarity	NPD8082	Approved
0.5739	Remote Similarity	NPD8085	Approved
0.5739	Remote Similarity	NPD8086	Approved
0.5739	Remote Similarity	NPD8139	Approved
0.5739	Remote Similarity	NPD8084	Approved
0.5739	Remote Similarity	NPD8083	Approved
0.5739	Remote Similarity	NPD8138	Approved
0.5726	Remote Similarity	NPD8393	Approved
0.5714	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD7736	Approved
0.569	Remote Similarity	NPD8275	Approved
0.569	Remote Similarity	NPD8276	Approved
0.5688	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8080	Discontinued
0.5652	Remote Similarity	NPD5344	Discontinued
0.5645	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8081	Approved
0.5632	Remote Similarity	NPD888	Phase 3
0.5632	Remote Similarity	NPD893	Approved
0.5632	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD891	Phase 3
0.5632	Remote Similarity	NPD892	Phase 3
0.5614	Remote Similarity	NPD7638	Approved
0.5603	Remote Similarity	NPD7139	Approved
0.5603	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD7140	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