NPASS Compound

Structure

NPC15095 OpenBabel07101718192D 45 52 0 0 1 0 0 0 0 0999 V2000 4.4727 -5.7311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7892 -4.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2919 -2.4270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -4.2883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1505 0.5711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4709 2.1711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0994 -5.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4233 -4.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3178 3.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7166 1.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3727 0.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7166 -1.7090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2749 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 -4.3588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6241 -3.6253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7021 2.5215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8985 1.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8985 -1.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2375 2.6203 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4332 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9885 -0.7643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -1.2366 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7166 0.1804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6734 0.0320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0803 1.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0803 0.1804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2593 0.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2364 1.2965 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5321 -3.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -3.8766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5553 -0.7643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.2919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6217 1.7573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4332 -1.5286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8985 -0.2919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1224 0.1444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0749 1.7317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6904 -2.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2077 -3.2136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.7643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8454 -2.2681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7724 -4.7909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3244 -2.9009 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 8 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 7 43 1 0 0 0 0 8 14 2 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 35 1 0 0 0 0 13 44 1 0 0 0 0 14 30 1 0 0 0 0 15 19 2 0 0 0 0 15 32 1 0 0 0 0 16 25 2 0 0 0 0 16 31 1 0 0 0 0 17 9 1 6 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 26 2 0 0 0 0 20 34 1 6 0 0 0 21 22 1 0 0 0 0 21 33 1 6 0 0 0 22 35 1 6 0 0 0 23 33 1 6 0 0 0 23 35 1 0 0 0 0 24 33 1 1 0 0 0 24 36 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 34 1 0 0 0 0 27 36 1 1 0 0 0 28 29 1 0 0 0 0 28 37 2 0 0 0 0 29 34 1 6 0 0 0 29 38 1 0 0 0 0 30 39 2 0 0 0 0 30 44 1 0 0 0 0 31 40 2 0 0 0 0 31 43 1 0 0 0 0 32 41 2 0 0 0 0 32 45 1 0 0 0 0 33 5 1 6 0 0 0 34 6 1 6 0 0 0 35 42 1 6 0 0 0 36 19 1 1 0 0 0 36 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.28
Volume:	620.781
LogP:	3.672
LogD:	2.944
LogS:	-4.884
# Rotatable Bonds:	7
TPSA:	133.27
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	6.697
Fsp3:	0.694
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293
MDCK Permeability:	0.00010716139513533562
Pgp-inhibitor:	1.0
Pgp-substrate:	0.301
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	70.32205963134766%
Volume Distribution (VD):	0.89
Pgp-substrate:	19.897857666015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.72
CYP2C19-substrate:	0.675
CYP2C9-inhibitor:	0.512
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	13.601
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.506
Human Hepatotoxicity (H-HT):	0.553
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.153
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC15095

Natural Product ID:	NPC15095
*Common Name:**	Sarcandrolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TUNYYJHZXJEAHU-AGBNGXIVSA-N
Standard InCHI:	InChI=1S/C36H42O9/c1-8-14(2)30(39)44-13-35(42)22-11-21(22)33(5)23(35)12-19-15(3)32(41)45-36(19)24(33)10-18-17-9-20(17)34(6)26(18)27(36)25(28(37)29(34)38)16(4)31(40)43-7/h8,17,20-24,27,29,38,42H,9-13H2,1-7H3/b14-8+,25-16-/t17-,20-,21-,22+,23-,24+,27+,29+,33+,34+,35+,36+/m1/s1
SMILES:	C/C=C(C)/C(=O)OC[C@@]1([C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(C)C(=O)O[C@@]31[C@H]2CC1=C2[C@@H]3/C(=C(C)/C(=O)OC)/C(=O)[C@@H]([C@@]2(C)[C@@H]2C[C@H]12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077056
PubChem CID:	44627380
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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27997206]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15190	Chloranthus fortunei	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3100.0	nM	PMID[514201]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7200.0	nM	PMID[514201]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	320.0	nM	PMID[514202]

☑ 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 NPC15095 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	283
0.1-0.2	1614
0.2-0.3	4796
0.3-0.4	9376
0.4-0.5	11884
0.5-0.6	6752
0.6-0.7	5992
0.7-0.8	1841
0.8-0.85	121
0.85-0.9	12
0.9-0.95	8
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC35109
0.9664	High Similarity	NPC220757
0.9664	High Similarity	NPC196921
0.9583	High Similarity	NPC34963
0.9504	High Similarity	NPC469673
0.9504	High Similarity	NPC58029
0.95	High Similarity	NPC241935
0.95	High Similarity	NPC279478
0.9426	High Similarity	NPC476823
0.8908	High Similarity	NPC17938
0.873	High Similarity	NPC469674
0.8699	High Similarity	NPC63186
0.8632	High Similarity	NPC470063
0.8583	High Similarity	NPC257457
0.8583	High Similarity	NPC311554
0.855	High Similarity	NPC25887
0.85	High Similarity	NPC284068
0.8492	Intermediate Similarity	NPC471407
0.8462	Intermediate Similarity	NPC475563
0.8462	Intermediate Similarity	NPC475134
0.843	Intermediate Similarity	NPC118638
0.8417	Intermediate Similarity	NPC148458
0.8417	Intermediate Similarity	NPC270958
0.8403	Intermediate Similarity	NPC202889
0.839	Intermediate Similarity	NPC475668
0.839	Intermediate Similarity	NPC473921
0.839	Intermediate Similarity	NPC475480
0.8387	Intermediate Similarity	NPC120724
0.8361	Intermediate Similarity	NPC475041
0.8359	Intermediate Similarity	NPC471855
0.8347	Intermediate Similarity	NPC239273
0.8347	Intermediate Similarity	NPC471854
0.8346	Intermediate Similarity	NPC470426
0.8346	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC476825
0.832	Intermediate Similarity	NPC8374
0.8319	Intermediate Similarity	NPC280782
0.8319	Intermediate Similarity	NPC475524
0.8319	Intermediate Similarity	NPC100267
0.8319	Intermediate Similarity	NPC71348
0.8306	Intermediate Similarity	NPC269642
0.8306	Intermediate Similarity	NPC162009
0.8306	Intermediate Similarity	NPC222688
0.8306	Intermediate Similarity	NPC257017
0.8306	Intermediate Similarity	NPC23786
0.8306	Intermediate Similarity	NPC470265
0.8305	Intermediate Similarity	NPC179642
0.8295	Intermediate Similarity	NPC476097
0.8295	Intermediate Similarity	NPC24599
0.8295	Intermediate Similarity	NPC470427
0.8295	Intermediate Similarity	NPC327664
0.8293	Intermediate Similarity	NPC109973
0.8264	Intermediate Similarity	NPC49492
0.8264	Intermediate Similarity	NPC196931
0.8264	Intermediate Similarity	NPC266728
0.825	Intermediate Similarity	NPC962
0.825	Intermediate Similarity	NPC250109
0.824	Intermediate Similarity	NPC473979
0.8231	Intermediate Similarity	NPC192334
0.8231	Intermediate Similarity	NPC60150
0.8226	Intermediate Similarity	NPC67569
0.8226	Intermediate Similarity	NPC52839
0.8217	Intermediate Similarity	NPC476824
0.8211	Intermediate Similarity	NPC264954
0.8203	Intermediate Similarity	NPC470880
0.8203	Intermediate Similarity	NPC134902
0.8189	Intermediate Similarity	NPC473253
0.8189	Intermediate Similarity	NPC470882
0.8189	Intermediate Similarity	NPC473265
0.8189	Intermediate Similarity	NPC287423
0.8182	Intermediate Similarity	NPC178289
0.8175	Intermediate Similarity	NPC8369
0.8167	Intermediate Similarity	NPC170487
0.816	Intermediate Similarity	NPC88326
0.816	Intermediate Similarity	NPC153700
0.8145	Intermediate Similarity	NPC474370
0.8145	Intermediate Similarity	NPC471126
0.8145	Intermediate Similarity	NPC145182
0.8145	Intermediate Similarity	NPC471128
0.8145	Intermediate Similarity	NPC157252
0.814	Intermediate Similarity	NPC254823
0.8136	Intermediate Similarity	NPC472825
0.8125	Intermediate Similarity	NPC236999
0.8125	Intermediate Similarity	NPC311534
0.812	Intermediate Similarity	NPC475414
0.812	Intermediate Similarity	NPC173172
0.8115	Intermediate Similarity	NPC190286
0.811	Intermediate Similarity	NPC222307
0.811	Intermediate Similarity	NPC473635
0.8103	Intermediate Similarity	NPC36688
0.8099	Intermediate Similarity	NPC474937
0.8095	Intermediate Similarity	NPC129992
0.8095	Intermediate Similarity	NPC11895
0.8095	Intermediate Similarity	NPC469789
0.8083	Intermediate Similarity	NPC214797
0.8083	Intermediate Similarity	NPC118860
0.8083	Intermediate Similarity	NPC231589
0.8067	Intermediate Similarity	NPC284828
0.8067	Intermediate Similarity	NPC173905
0.8067	Intermediate Similarity	NPC5475
0.8067	Intermediate Similarity	NPC241927
0.8067	Intermediate Similarity	NPC472216
0.8067	Intermediate Similarity	NPC258543
0.8065	Intermediate Similarity	NPC9674
0.8065	Intermediate Similarity	NPC5989
0.8065	Intermediate Similarity	NPC5991
0.8065	Intermediate Similarity	NPC19028
0.8065	Intermediate Similarity	NPC469380
0.8065	Intermediate Similarity	NPC275696
0.8065	Intermediate Similarity	NPC471108
0.8065	Intermediate Similarity	NPC255081
0.8065	Intermediate Similarity	NPC22628
0.8065	Intermediate Similarity	NPC5292
0.8051	Intermediate Similarity	NPC475176
0.8051	Intermediate Similarity	NPC475294
0.8051	Intermediate Similarity	NPC131665
0.8051	Intermediate Similarity	NPC255387
0.8049	Intermediate Similarity	NPC470493
0.8049	Intermediate Similarity	NPC286528
0.8049	Intermediate Similarity	NPC167606
0.8049	Intermediate Similarity	NPC140055
0.8049	Intermediate Similarity	NPC470492
0.8049	Intermediate Similarity	NPC312824
0.8049	Intermediate Similarity	NPC20302
0.8049	Intermediate Similarity	NPC183580
0.8047	Intermediate Similarity	NPC42399
0.8033	Intermediate Similarity	NPC474872
0.8031	Intermediate Similarity	NPC145238
0.8031	Intermediate Similarity	NPC81736
0.8031	Intermediate Similarity	NPC473255
0.8031	Intermediate Similarity	NPC172154
0.8017	Intermediate Similarity	NPC475391
0.8017	Intermediate Similarity	NPC151216
0.8017	Intermediate Similarity	NPC101825
0.8017	Intermediate Similarity	NPC221511
0.8017	Intermediate Similarity	NPC170212
0.8017	Intermediate Similarity	NPC17138
0.8017	Intermediate Similarity	NPC221144
0.8017	Intermediate Similarity	NPC265499
0.8017	Intermediate Similarity	NPC236217
0.8017	Intermediate Similarity	NPC215643
0.8017	Intermediate Similarity	NPC89227
0.8016	Intermediate Similarity	NPC27335
0.8016	Intermediate Similarity	NPC170538
0.8015	Intermediate Similarity	NPC88668
0.8	Intermediate Similarity	NPC19336
0.8	Intermediate Similarity	NPC474585
0.8	Intermediate Similarity	NPC470312
0.8	Intermediate Similarity	NPC5284
0.8	Intermediate Similarity	NPC471406
0.8	Intermediate Similarity	NPC79579
0.8	Intermediate Similarity	NPC76084
0.8	Intermediate Similarity	NPC472004
0.8	Intermediate Similarity	NPC185876
0.7984	Intermediate Similarity	NPC709
0.7984	Intermediate Similarity	NPC124676
0.7984	Intermediate Similarity	NPC146280
0.7984	Intermediate Similarity	NPC472758
0.7984	Intermediate Similarity	NPC270109
0.7984	Intermediate Similarity	NPC472397
0.7984	Intermediate Similarity	NPC153440
0.7984	Intermediate Similarity	NPC475372
0.7984	Intermediate Similarity	NPC171905
0.7984	Intermediate Similarity	NPC471125
0.7984	Intermediate Similarity	NPC50774
0.7983	Intermediate Similarity	NPC88701
0.7969	Intermediate Similarity	NPC293112
0.7967	Intermediate Similarity	NPC176840
0.7966	Intermediate Similarity	NPC186668
0.7966	Intermediate Similarity	NPC196528
0.7955	Intermediate Similarity	NPC471234
0.7953	Intermediate Similarity	NPC27363
0.7953	Intermediate Similarity	NPC472399
0.7951	Intermediate Similarity	NPC317210
0.7951	Intermediate Similarity	NPC194100
0.7951	Intermediate Similarity	NPC71889
0.7951	Intermediate Similarity	NPC472926
0.7949	Intermediate Similarity	NPC112009
0.7949	Intermediate Similarity	NPC180204
0.7949	Intermediate Similarity	NPC472821
0.7949	Intermediate Similarity	NPC476237
0.7939	Intermediate Similarity	NPC231240
0.7937	Intermediate Similarity	NPC310511
0.7937	Intermediate Similarity	NPC472000
0.7937	Intermediate Similarity	NPC471999
0.7937	Intermediate Similarity	NPC46570
0.7934	Intermediate Similarity	NPC174471
0.7934	Intermediate Similarity	NPC474871
0.7934	Intermediate Similarity	NPC43775
0.7934	Intermediate Similarity	NPC470076
0.7934	Intermediate Similarity	NPC260786
0.7934	Intermediate Similarity	NPC96739
0.7931	Intermediate Similarity	NPC247701
0.7931	Intermediate Similarity	NPC268829
0.7931	Intermediate Similarity	NPC222875
0.7931	Intermediate Similarity	NPC25177
0.7931	Intermediate Similarity	NPC295110
0.7923	Intermediate Similarity	NPC473593
0.7923	Intermediate Similarity	NPC104382
0.7923	Intermediate Similarity	NPC476966

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 NPC15095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	1804
0.2-0.3	3900
0.3-0.4	2128
0.4-0.5	609
0.5-0.6	232
0.6-0.7	150
0.7-0.8	86
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8049	Intermediate Similarity	NPD7115	Discovery
0.8017	Intermediate Similarity	NPD8297	Approved
0.7951	Intermediate Similarity	NPD4632	Approved
0.7857	Intermediate Similarity	NPD6319	Approved
0.7829	Intermediate Similarity	NPD7507	Approved
0.7812	Intermediate Similarity	NPD7604	Phase 2
0.7787	Intermediate Similarity	NPD6650	Approved
0.7787	Intermediate Similarity	NPD6649	Approved
0.7769	Intermediate Similarity	NPD6372	Approved
0.7769	Intermediate Similarity	NPD6373	Approved
0.7759	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD7640	Approved
0.7686	Intermediate Similarity	NPD6899	Approved
0.7686	Intermediate Similarity	NPD7320	Approved
0.7686	Intermediate Similarity	NPD6881	Approved
0.7667	Intermediate Similarity	NPD6402	Approved
0.7667	Intermediate Similarity	NPD7128	Approved
0.7667	Intermediate Similarity	NPD6008	Approved
0.7667	Intermediate Similarity	NPD6675	Approved
0.7667	Intermediate Similarity	NPD5739	Approved
0.7656	Intermediate Similarity	NPD8033	Approved
0.7652	Intermediate Similarity	NPD7319	Approved
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7634	Intermediate Similarity	NPD7078	Approved
0.7623	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6009	Approved
0.7615	Intermediate Similarity	NPD7492	Approved
0.7603	Intermediate Similarity	NPD5697	Approved
0.7581	Intermediate Similarity	NPD6882	Approved
0.7578	Intermediate Similarity	NPD8377	Approved
0.7578	Intermediate Similarity	NPD8294	Approved
0.7578	Intermediate Similarity	NPD6054	Approved
0.7576	Intermediate Similarity	NPD7736	Approved
0.7561	Intermediate Similarity	NPD7102	Approved
0.7561	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7290	Approved
0.7561	Intermediate Similarity	NPD6883	Approved
0.7559	Intermediate Similarity	NPD7327	Approved
0.7559	Intermediate Similarity	NPD7328	Approved
0.7557	Intermediate Similarity	NPD6616	Approved
0.7541	Intermediate Similarity	NPD6011	Approved
0.7521	Intermediate Similarity	NPD6083	Phase 2
0.7521	Intermediate Similarity	NPD6084	Phase 2
0.7519	Intermediate Similarity	NPD8378	Approved
0.7519	Intermediate Similarity	NPD5983	Phase 2
0.7519	Intermediate Similarity	NPD8296	Approved
0.7519	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD8335	Approved
0.7519	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD6013	Approved
0.748	Intermediate Similarity	NPD6012	Approved
0.748	Intermediate Similarity	NPD6014	Approved
0.7462	Intermediate Similarity	NPD6370	Approved
0.7459	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5701	Approved
0.7442	Intermediate Similarity	NPD6059	Approved
0.7424	Intermediate Similarity	NPD6336	Discontinued
0.7419	Intermediate Similarity	NPD6371	Approved
0.7414	Intermediate Similarity	NPD6001	Approved
0.7398	Intermediate Similarity	NPD6686	Approved
0.7385	Intermediate Similarity	NPD6015	Approved
0.7385	Intermediate Similarity	NPD6016	Approved
0.736	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5988	Approved
0.7317	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5696	Approved
0.728	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7252	Intermediate Similarity	NPD7503	Approved
0.725	Intermediate Similarity	NPD5286	Approved
0.725	Intermediate Similarity	NPD4696	Approved
0.725	Intermediate Similarity	NPD5285	Approved
0.7241	Intermediate Similarity	NPD5693	Phase 1
0.7227	Intermediate Similarity	NPD4755	Approved
0.7203	Intermediate Similarity	NPD5695	Phase 3
0.719	Intermediate Similarity	NPD5223	Approved
0.7179	Intermediate Similarity	NPD6399	Phase 3
0.7177	Intermediate Similarity	NPD6412	Phase 2
0.7167	Intermediate Similarity	NPD4225	Approved
0.7165	Intermediate Similarity	NPD6053	Discontinued
0.7154	Intermediate Similarity	NPD6335	Approved
0.7154	Intermediate Similarity	NPD5141	Approved
0.7132	Intermediate Similarity	NPD6274	Approved
0.7131	Intermediate Similarity	NPD5224	Approved
0.7131	Intermediate Similarity	NPD7632	Discontinued
0.7131	Intermediate Similarity	NPD5226	Approved
0.7131	Intermediate Similarity	NPD5225	Approved
0.7131	Intermediate Similarity	NPD4633	Approved
0.7121	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4700	Approved
0.7099	Intermediate Similarity	NPD7100	Approved
0.7099	Intermediate Similarity	NPD7101	Approved
0.7077	Intermediate Similarity	NPD6317	Approved
0.7073	Intermediate Similarity	NPD5174	Approved
0.7073	Intermediate Similarity	NPD5175	Approved
0.7069	Intermediate Similarity	NPD6673	Approved
0.7069	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD6080	Approved
0.7069	Intermediate Similarity	NPD6904	Approved
0.7059	Intermediate Similarity	NPD5210	Approved
0.7059	Intermediate Similarity	NPD6033	Approved
0.7059	Intermediate Similarity	NPD4629	Approved
0.7034	Intermediate Similarity	NPD4202	Approved
0.7023	Intermediate Similarity	NPD6314	Approved
0.7023	Intermediate Similarity	NPD6313	Approved
0.7015	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.6984	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5737	Approved
0.6983	Remote Similarity	NPD6672	Approved
0.6983	Remote Similarity	NPD6903	Approved
0.6977	Remote Similarity	NPD8133	Approved
0.6975	Remote Similarity	NPD7748	Approved
0.696	Remote Similarity	NPD4768	Approved
0.696	Remote Similarity	NPD4767	Approved
0.6957	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD7146	Approved
0.6957	Remote Similarity	NPD7521	Approved
0.6957	Remote Similarity	NPD5330	Approved
0.6957	Remote Similarity	NPD6684	Approved
0.6957	Remote Similarity	NPD3618	Phase 1
0.6957	Remote Similarity	NPD7334	Approved
0.6949	Remote Similarity	NPD6079	Approved
0.6942	Remote Similarity	NPD5173	Approved
0.6942	Remote Similarity	NPD7902	Approved
0.6935	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6906	Remote Similarity	NPD7260	Phase 2
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5329	Approved
0.687	Remote Similarity	NPD6868	Approved
0.6866	Remote Similarity	NPD6909	Approved
0.6866	Remote Similarity	NPD6908	Approved
0.685	Remote Similarity	NPD5128	Approved
0.6838	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6098	Approved
0.6807	Remote Similarity	NPD6050	Approved
0.6807	Remote Similarity	NPD7515	Phase 2
0.6797	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3666	Approved
0.6783	Remote Similarity	NPD3133	Approved
0.6783	Remote Similarity	NPD3665	Phase 1
0.6783	Remote Similarity	NPD4197	Approved
0.6783	Remote Similarity	NPD4786	Approved
0.6774	Remote Similarity	NPD5344	Discontinued
0.6765	Remote Similarity	NPD6067	Discontinued
0.6744	Remote Similarity	NPD5169	Approved
0.6744	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5135	Approved
0.6738	Remote Similarity	NPD6845	Suspended
0.6723	Remote Similarity	NPD5692	Phase 3
0.6723	Remote Similarity	NPD46	Approved
0.6723	Remote Similarity	NPD6698	Approved
0.6723	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7900	Approved
0.6692	Remote Similarity	NPD5217	Approved
0.6692	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5215	Approved
0.6692	Remote Similarity	NPD5216	Approved
0.6692	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5281	Approved
0.6639	Remote Similarity	NPD6051	Approved
0.6621	Remote Similarity	NPD6333	Approved
0.6621	Remote Similarity	NPD6334	Approved
0.6609	Remote Similarity	NPD4223	Phase 3
0.6609	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3667	Approved
0.6609	Remote Similarity	NPD4221	Approved
0.6596	Remote Similarity	NPD5956	Approved
0.6583	Remote Similarity	NPD5207	Approved
0.6581	Remote Similarity	NPD1694	Approved
0.6565	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5208	Approved
0.6541	Remote Similarity	NPD5167	Approved
0.6532	Remote Similarity	NPD5959	Approved
0.6525	Remote Similarity	NPD5280	Approved
0.6525	Remote Similarity	NPD5279	Phase 3

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