NPASS Compound

Structure

NPC471861 OpenBabel07101719402D 56 65 0 0 1 0 0 0 0 0999 V2000 2.8514 1.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 2.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8514 4.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7796 -0.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7796 0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9136 -1.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9136 0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0475 -0.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5561 -2.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7371 -0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1548 -1.1979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5506 -2.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7317 -0.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7481 -0.2843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5834 0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3218 2.1168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9854 1.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 3.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5834 3.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 4.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3155 2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1444 -0.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1494 -1.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0475 0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4495 0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1384 -1.5115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3272 2.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1815 0.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8514 2.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5834 2.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7174 3.6994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7536 -0.1798 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 -1.4863 1.3383 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7174 1.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4495 1.6994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3523 0.8383 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8514 3.1994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1193 3.1994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9854 3.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1329 -1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 4.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1658 -0.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3818 2.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1815 1.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1499 -0.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3468 0.7337 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 4 44 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 29 2 0 0 0 0 9 29 1 0 0 0 0 10 13 1 0 0 0 0 10 28 2 0 0 0 0 11 14 2 0 0 0 0 11 28 1 0 0 0 0 12 15 1 0 0 0 0 12 28 1 0 0 0 0 13 31 2 0 0 0 0 14 31 1 0 0 0 0 15 38 1 0 0 0 0 16 19 1 0 0 0 0 16 30 2 0 0 0 0 17 21 1 0 0 0 0 17 33 1 0 0 0 0 18 20 2 0 0 0 0 18 35 1 0 0 0 0 19 41 1 0 0 0 0 20 45 1 0 0 0 0 22 30 1 0 0 0 0 22 34 1 0 0 0 0 23 36 1 0 0 0 0 23 37 1 0 0 0 0 25 45 1 0 0 0 0 25 46 1 0 0 0 0 26 42 1 0 0 0 0 26 53 1 0 0 0 0 27 43 1 0 0 0 0 27 54 1 0 0 0 0 30 42 1 0 0 0 0 31 48 1 0 0 0 0 32 24 1 1 0 0 0 32 33 1 0 0 0 0 32 39 1 0 0 0 0 33 45 1 1 0 0 0 34 29 1 6 0 0 0 34 53 1 0 0 0 0 35 41 1 1 0 0 0 35 44 1 0 0 0 0 36 41 1 1 0 0 0 36 42 1 0 0 0 0 37 44 1 6 0 0 0 37 49 1 0 0 0 0 38 50 2 0 0 0 0 38 55 1 0 0 0 0 39 51 2 0 0 0 0 39 56 1 0 0 0 0 40 43 1 1 0 0 0 40 47 1 0 0 0 0 40 52 1 0 0 0 0 41 1 1 1 0 0 0 42 2 1 6 0 0 0 43 3 1 1 0 0 0 43 55 1 0 0 0 0 44 46 1 6 0 0 0 45 46 1 6 0 0 0 46 21 1 1 0 0 0 47 24 1 6 0 0 0 47 54 1 0 0 0 0 47 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	764.39
Volume:	788.651
LogP:	5.353
LogD:	3.551
LogS:	-4.849
# Rotatable Bonds:	7
TPSA:	131.75
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	10
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	6.553
Fsp3:	0.617
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	2.279029467899818e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.808
30% Bioavailability (F30%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	96.09343719482422%
Volume Distribution (VD):	0.981
Pgp-substrate:	4.310618877410889%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.215
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	8.209
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.888
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.78
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC471861

Natural Product ID:	NPC471861
*Common Name:**	NCDMXKSFHSNCLP-QJQHGWFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NCDMXKSFHSNCLP-QJQHGWFVSA-N
Standard InCHI:	InChI=1S/C47H56O9/c1-41-19-16-30-22-34(29-8-6-5-7-9-29)53-26-42(30,2)36(41)23-37(49)44(4)35(41)18-20-45-25-46(44,45)21-17-33(45)32-24-47(56-39(32)51)40(52)43(3,27-54-47)55-38(50)15-12-28-10-13-31(48)14-11-28/h5-11,13-14,16,18,20,32-37,40,48-49,52H,12,15,17,19,21-27H2,1-4H3/t32-,33-,34-,35+,36+,37+,40+,41+,42-,43-,44-,45+,46+,47+/m0/s1
SMILES:	O=C(O[C@@]1(C)CO[C@@]2([C@@H]1O)OC(=O)[C@@H](C2)[C@@H]1CC[C@@]23[C@]1(C=C[C@H]1[C@@]3(C)[C@H](O)C[C@@H]3[C@]1(C)CC=C1[C@]3(C)CO[C@@H](C1)c1ccccc1)C2)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261939
PubChem CID:	90676175
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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
EC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	EC50	=	9.8	microg/cm2	PMID[515902]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	61.8	%	PMID[515902]

☑ 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 NPC471861 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	378
0.1-0.2	1327
0.2-0.3	2912
0.3-0.4	5260
0.4-0.5	9527
0.5-0.6	13200
0.6-0.7	8703
0.7-0.8	1357
0.8-0.85	24
0.85-0.9	4
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC471860
0.9554	High Similarity	NPC471850
0.949	High Similarity	NPC471858
0.9317	High Similarity	NPC471859
0.881	High Similarity	NPC475244
0.8797	High Similarity	NPC261659
0.8671	High Similarity	NPC253591
0.8639	High Similarity	NPC473467
0.8639	High Similarity	NPC475197
0.8608	High Similarity	NPC475561
0.8608	High Similarity	NPC475417
0.858	High Similarity	NPC477617
0.8563	High Similarity	NPC469458
0.8563	High Similarity	NPC88176
0.8563	High Similarity	NPC149002
0.8563	High Similarity	NPC469396
0.8516	High Similarity	NPC471856
0.8506	High Similarity	NPC79921
0.8485	Intermediate Similarity	NPC269668
0.8471	Intermediate Similarity	NPC96447
0.8452	Intermediate Similarity	NPC469419
0.8452	Intermediate Similarity	NPC469459
0.8452	Intermediate Similarity	NPC471862
0.843	Intermediate Similarity	NPC475613
0.8377	Intermediate Similarity	NPC262324
0.8377	Intermediate Similarity	NPC243893
0.8363	Intermediate Similarity	NPC148185
0.8333	Intermediate Similarity	NPC77310
0.8313	Intermediate Similarity	NPC470330
0.8276	Intermediate Similarity	NPC260300
0.8272	Intermediate Similarity	NPC162569
0.8272	Intermediate Similarity	NPC116292
0.8272	Intermediate Similarity	NPC35160
0.8272	Intermediate Similarity	NPC35097
0.8272	Intermediate Similarity	NPC87630
0.8272	Intermediate Similarity	NPC179128
0.8272	Intermediate Similarity	NPC267469
0.825	Intermediate Similarity	NPC320734
0.8225	Intermediate Similarity	NPC161151
0.8221	Intermediate Similarity	NPC472657
0.8221	Intermediate Similarity	NPC472658
0.8217	Intermediate Similarity	NPC164743
0.8214	Intermediate Similarity	NPC117943
0.8214	Intermediate Similarity	NPC293568
0.8214	Intermediate Similarity	NPC477627
0.821	Intermediate Similarity	NPC279442
0.8208	Intermediate Similarity	NPC195972
0.8193	Intermediate Similarity	NPC10945
0.8171	Intermediate Similarity	NPC80360
0.816	Intermediate Similarity	NPC327962
0.8148	Intermediate Similarity	NPC120728
0.814	Intermediate Similarity	NPC266545
0.814	Intermediate Similarity	NPC202428
0.8129	Intermediate Similarity	NPC471864
0.8125	Intermediate Similarity	NPC195114
0.8125	Intermediate Similarity	NPC25491
0.8092	Intermediate Similarity	NPC179240
0.8086	Intermediate Similarity	NPC472936
0.8086	Intermediate Similarity	NPC472938
0.8086	Intermediate Similarity	NPC472937
0.8081	Intermediate Similarity	NPC177362
0.8081	Intermediate Similarity	NPC185498
0.8079	Intermediate Similarity	NPC188217
0.807	Intermediate Similarity	NPC265600
0.8068	Intermediate Similarity	NPC469418
0.8063	Intermediate Similarity	NPC204644
0.8059	Intermediate Similarity	NPC326278
0.805	Intermediate Similarity	NPC172311
0.8049	Intermediate Similarity	NPC117346
0.8049	Intermediate Similarity	NPC240592
0.8049	Intermediate Similarity	NPC472548
0.8049	Intermediate Similarity	NPC472939
0.8046	Intermediate Similarity	NPC149502
0.8046	Intermediate Similarity	NPC271755
0.8046	Intermediate Similarity	NPC222665
0.8046	Intermediate Similarity	NPC254071
0.8046	Intermediate Similarity	NPC13989
0.8038	Intermediate Similarity	NPC324262
0.8038	Intermediate Similarity	NPC62800
0.8037	Intermediate Similarity	NPC325032
0.8037	Intermediate Similarity	NPC477483
0.8025	Intermediate Similarity	NPC208293
0.8024	Intermediate Similarity	NPC472807
0.8023	Intermediate Similarity	NPC200726
0.8023	Intermediate Similarity	NPC108191
0.8023	Intermediate Similarity	NPC93685
0.8023	Intermediate Similarity	NPC306475
0.8012	Intermediate Similarity	NPC257847
0.8012	Intermediate Similarity	NPC202391
0.8012	Intermediate Similarity	NPC14294
0.8012	Intermediate Similarity	NPC327694
0.8012	Intermediate Similarity	NPC116759
0.8012	Intermediate Similarity	NPC109990
0.8012	Intermediate Similarity	NPC296659
0.8	Intermediate Similarity	NPC471871
0.8	Intermediate Similarity	NPC119252
0.8	Intermediate Similarity	NPC152424
0.8	Intermediate Similarity	NPC100465
0.7988	Intermediate Similarity	NPC473719
0.7988	Intermediate Similarity	NPC96599
0.7987	Intermediate Similarity	NPC470617
0.7987	Intermediate Similarity	NPC470616
0.7977	Intermediate Similarity	NPC286809
0.7965	Intermediate Similarity	NPC318472
0.7955	Intermediate Similarity	NPC469438
0.7953	Intermediate Similarity	NPC477491
0.7953	Intermediate Similarity	NPC145847
0.7952	Intermediate Similarity	NPC472549
0.7944	Intermediate Similarity	NPC299855
0.7944	Intermediate Similarity	NPC96194
0.7941	Intermediate Similarity	NPC91634
0.7941	Intermediate Similarity	NPC150943
0.7941	Intermediate Similarity	NPC130489
0.7941	Intermediate Similarity	NPC268718
0.7941	Intermediate Similarity	NPC208676
0.7939	Intermediate Similarity	NPC477905
0.7937	Intermediate Similarity	NPC3218
0.7937	Intermediate Similarity	NPC27518
0.7937	Intermediate Similarity	NPC304110
0.7931	Intermediate Similarity	NPC471870
0.7927	Intermediate Similarity	NPC95990
0.7925	Intermediate Similarity	NPC139243
0.7925	Intermediate Similarity	NPC248287
0.7925	Intermediate Similarity	NPC234548
0.7925	Intermediate Similarity	NPC116742
0.7923	Intermediate Similarity	NPC475299
0.7917	Intermediate Similarity	NPC476784
0.7914	Intermediate Similarity	NPC473147
0.791	Intermediate Similarity	NPC469397
0.7907	Intermediate Similarity	NPC100420
0.7907	Intermediate Similarity	NPC120012
0.7904	Intermediate Similarity	NPC154675
0.7901	Intermediate Similarity	NPC477207
0.7901	Intermediate Similarity	NPC194938
0.7901	Intermediate Similarity	NPC189704
0.7898	Intermediate Similarity	NPC124828
0.7895	Intermediate Similarity	NPC288149
0.7895	Intermediate Similarity	NPC266365
0.7892	Intermediate Similarity	NPC289021
0.7892	Intermediate Similarity	NPC158546
0.7888	Intermediate Similarity	NPC272907
0.7888	Intermediate Similarity	NPC2681
0.7882	Intermediate Similarity	NPC275477
0.7879	Intermediate Similarity	NPC161955
0.7879	Intermediate Similarity	NPC477206
0.7877	Intermediate Similarity	NPC102367
0.787	Intermediate Similarity	NPC309991
0.787	Intermediate Similarity	NPC475378
0.787	Intermediate Similarity	NPC237946
0.787	Intermediate Similarity	NPC326328
0.787	Intermediate Similarity	NPC32373
0.787	Intermediate Similarity	NPC471138
0.787	Intermediate Similarity	NPC323356
0.7866	Intermediate Similarity	NPC246229
0.7866	Intermediate Similarity	NPC474991
0.7866	Intermediate Similarity	NPC191899
0.7862	Intermediate Similarity	NPC198621
0.7862	Intermediate Similarity	NPC475482
0.7862	Intermediate Similarity	NPC22676
0.7862	Intermediate Similarity	NPC216940
0.7861	Intermediate Similarity	NPC222531
0.7861	Intermediate Similarity	NPC469420
0.7861	Intermediate Similarity	NPC40138
0.7857	Intermediate Similarity	NPC318447
0.7857	Intermediate Similarity	NPC476067
0.7857	Intermediate Similarity	NPC322048
0.7857	Intermediate Similarity	NPC469417
0.7857	Intermediate Similarity	NPC475121
0.7844	Intermediate Similarity	NPC34066
0.7841	Intermediate Similarity	NPC469777
0.7841	Intermediate Similarity	NPC135334
0.7841	Intermediate Similarity	NPC469772
0.7841	Intermediate Similarity	NPC32723
0.7841	Intermediate Similarity	NPC469776
0.7841	Intermediate Similarity	NPC100925
0.7841	Intermediate Similarity	NPC469778
0.7841	Intermediate Similarity	NPC295941
0.7841	Intermediate Similarity	NPC469774
0.7841	Intermediate Similarity	NPC469773
0.7841	Intermediate Similarity	NPC469775
0.784	Intermediate Similarity	NPC478250
0.7836	Intermediate Similarity	NPC96593
0.7836	Intermediate Similarity	NPC478073
0.7833	Intermediate Similarity	NPC473205
0.7833	Intermediate Similarity	NPC186746
0.7833	Intermediate Similarity	NPC473776
0.7831	Intermediate Similarity	NPC247219
0.7829	Intermediate Similarity	NPC21956
0.7824	Intermediate Similarity	NPC187205
0.7824	Intermediate Similarity	NPC207584
0.7824	Intermediate Similarity	NPC206641
0.7824	Intermediate Similarity	NPC19947
0.7824	Intermediate Similarity	NPC208651
0.7818	Intermediate Similarity	NPC469448
0.7818	Intermediate Similarity	NPC127046
0.7816	Intermediate Similarity	NPC477488
0.7811	Intermediate Similarity	NPC38699
0.7811	Intermediate Similarity	NPC469399
0.7811	Intermediate Similarity	NPC475484
0.7809	Intermediate Similarity	NPC11062

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 NPC471861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	793
0.2-0.3	1854
0.3-0.4	2796
0.4-0.5	2129
0.5-0.6	1003
0.6-0.7	237
0.7-0.8	24
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
0.8081	Intermediate Similarity	NPD7228	Approved
0.8023	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7697	Intermediate Similarity	NPD7240	Approved
0.7697	Intermediate Similarity	NPD7685	Pre-registration
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7571	Intermediate Similarity	NPD7799	Discontinued
0.7544	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7486	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6663	Approved
0.7455	Intermediate Similarity	NPD8166	Discontinued
0.7419	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7680	Approved
0.7342	Intermediate Similarity	NPD5736	Approved
0.7322	Intermediate Similarity	NPD8312	Approved
0.7322	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD6190	Approved
0.7301	Intermediate Similarity	NPD7097	Phase 1
0.7297	Intermediate Similarity	NPD8434	Phase 2
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD7028	Phase 2
0.7262	Intermediate Similarity	NPD7236	Approved
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7239	Suspended
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3764	Approved
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7088	Intermediate Similarity	NPD3751	Discontinued
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7035	Intermediate Similarity	NPD6273	Approved
0.7022	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7074	Phase 3
0.7005	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6971	Remote Similarity	NPD4380	Phase 2
0.6964	Remote Similarity	NPD6002	Phase 3
0.6964	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5762	Approved
0.6964	Remote Similarity	NPD6004	Phase 3
0.6964	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6005	Phase 3
0.6964	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD7699	Phase 2
0.6959	Remote Similarity	NPD7700	Phase 2
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD7054	Approved
0.6954	Remote Similarity	NPD7497	Discontinued
0.6954	Remote Similarity	NPD7435	Discontinued
0.6951	Remote Similarity	NPD8032	Phase 2
0.6946	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD2932	Approved
0.6943	Remote Similarity	NPD3019	Approved
0.6943	Remote Similarity	NPD5126	Approved
0.6943	Remote Similarity	NPD5125	Phase 3
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7473	Discontinued
0.6935	Remote Similarity	NPD6559	Discontinued
0.6933	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7075	Discontinued
0.6923	Remote Similarity	NPD7741	Discontinued
0.6919	Remote Similarity	NPD7472	Approved
0.6915	Remote Similarity	NPD8407	Phase 2
0.691	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4140	Approved
0.6905	Remote Similarity	NPD6099	Approved
0.6905	Remote Similarity	NPD6100	Approved
0.6902	Remote Similarity	NPD3818	Discontinued
0.6898	Remote Similarity	NPD7808	Phase 3
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.6882	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7783	Phase 2
0.6881	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6232	Discontinued
0.6868	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD5735	Approved
0.6865	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7930	Approved
0.6859	Remote Similarity	NPD8361	Approved
0.6859	Remote Similarity	NPD8360	Approved
0.6855	Remote Similarity	NPD3092	Approved
0.6854	Remote Similarity	NPD7819	Suspended
0.6845	Remote Similarity	NPD6765	Approved
0.6845	Remote Similarity	NPD6764	Approved
0.6845	Remote Similarity	NPD8368	Discontinued
0.6845	Remote Similarity	NPD7251	Discontinued
0.6836	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7874	Approved
0.6829	Remote Similarity	NPD7095	Approved
0.6809	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6776	Approved
0.6802	Remote Similarity	NPD6779	Approved
0.6802	Remote Similarity	NPD6782	Approved
0.6802	Remote Similarity	NPD6781	Approved
0.6802	Remote Similarity	NPD6780	Approved
0.6802	Remote Similarity	NPD6778	Approved
0.6802	Remote Similarity	NPD6777	Approved
0.68	Remote Similarity	NPD7999	Approved
0.6793	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6166	Phase 2
0.6791	Remote Similarity	NPD6797	Phase 2
0.6788	Remote Similarity	NPD6798	Discontinued
0.6788	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6674	Discontinued
0.6784	Remote Similarity	NPD7698	Approved
0.6784	Remote Similarity	NPD7696	Phase 3
0.6784	Remote Similarity	NPD7697	Approved
0.6782	Remote Similarity	NPD8151	Discontinued
0.6778	Remote Similarity	NPD7057	Phase 3
0.6778	Remote Similarity	NPD7058	Phase 2
0.6771	Remote Similarity	NPD8435	Approved
0.676	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7870	Phase 2
0.675	Remote Similarity	NPD7871	Phase 2
0.6747	Remote Similarity	NPD6233	Phase 2
0.6744	Remote Similarity	NPD7003	Approved
0.6744	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4110	Phase 3
0.6733	Remote Similarity	NPD7701	Phase 2
0.6726	Remote Similarity	NPD6653	Approved
0.6721	Remote Similarity	NPD6959	Discontinued
0.6717	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7801	Approved
0.6709	Remote Similarity	NPD3091	Approved
0.6707	Remote Similarity	NPD2861	Phase 2
0.6707	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4060	Phase 1
0.6707	Remote Similarity	NPD3620	Phase 2
0.6706	Remote Similarity	NPD2438	Suspended
0.6705	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6784	Approved
0.6702	Remote Similarity	NPD6785	Approved
0.6686	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2534	Approved
0.6686	Remote Similarity	NPD2532	Approved
0.6686	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD4582	Approved
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4583	Approved
0.665	Remote Similarity	NPD6823	Phase 2
0.6648	Remote Similarity	NPD7411	Suspended
0.6648	Remote Similarity	NPD3749	Approved
0.6629	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6353	Approved
0.6626	Remote Similarity	NPD8651	Approved
0.6617	Remote Similarity	NPD4004	Approved
0.6617	Remote Similarity	NPD4002	Approved
0.6611	Remote Similarity	NPD1934	Approved
0.6611	Remote Similarity	NPD6801	Discontinued
0.6609	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1608	Approved
0.6597	Remote Similarity	NPD7312	Approved
0.6597	Remote Similarity	NPD7313	Approved
0.6597	Remote Similarity	NPD7310	Approved
0.6597	Remote Similarity	NPD7311	Approved
0.6595	Remote Similarity	NPD7315	Approved
0.6593	Remote Similarity	NPD7768	Phase 2
0.6592	Remote Similarity	NPD6599	Discontinued
0.6587	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3023	Approved
0.6584	Remote Similarity	NPD3026	Approved
0.6576	Remote Similarity	NPD5494	Approved
0.6575	Remote Similarity	NPD1465	Phase 2
0.6568	Remote Similarity	NPD230	Phase 1
0.6566	Remote Similarity	NPD4908	Phase 1
0.6566	Remote Similarity	NPD8485	Approved
0.6562	Remote Similarity	NPD7309	Approved
0.6562	Remote Similarity	NPD3024	Approved
0.6562	Remote Similarity	NPD3025	Approved
0.6561	Remote Similarity	NPD2629	Approved
0.6555	Remote Similarity	NPD8404	Phase 2

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