NPASS Compound

Structure

NPC283343 OpenBabel07101719152D 41 45 0 0 1 0 0 0 0 0999 V2000 -4.1459 4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8042 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1796 3.7015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1371 3.7015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8380 -2.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7954 -2.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9750 3.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1459 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3167 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9750 2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4875 -1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6583 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1459 -1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6583 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4875 1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4875 2.3936 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1459 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3167 -1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 -0.4787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8292 -0.4787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6583 0.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3167 -0.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9750 -1.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4875 -0.4787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 0.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1459 1.4362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3167 2.8723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 8 33 1 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 18 26 1 0 0 0 0 18 34 1 0 0 0 0 19 36 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 1 0 0 0 23 31 1 0 0 0 0 23 32 1 6 0 0 0 24 32 1 6 0 0 0 24 33 1 0 0 0 0 25 31 1 0 0 0 0 25 37 1 6 0 0 0 26 35 1 1 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 1 0 0 0 27 39 1 0 0 0 0 28 30 1 0 0 0 0 28 41 1 6 0 0 0 29 40 2 0 0 0 0 29 41 1 0 0 0 0 32 7 1 6 0 0 0 33 34 1 1 0 0 0 34 9 1 1 0 0 0 35 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.41
Volume:	615.966
LogP:	5.002
LogD:	4.388
LogS:	-4.447
# Rotatable Bonds:	4
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.2
Synthetic Accessibility Score:	5.293
Fsp3:	0.857
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:	-5.102
MDCK Permeability:	3.734293204615824e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	91.30660247802734%
Volume Distribution (VD):	1.0
Pgp-substrate:	5.341629505157471%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	5.192
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.648
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.493
Carcinogencity:	0.021
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC283343

Natural Product ID:	NPC283343
*Common Name:**	(+)-Barringtogenol B
IUPAC Name:	[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4,5,10-trihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (Z)-2-methylbut-2-enoate
Synonyms:	Barringtogenol-C 21-Angelate
Standard InCHIKey:	SJSCBAFROHXGCX-MAVWQDHUSA-N
Standard InCHI:	InChI=1S/C35H56O6/c1-10-20(2)29(40)41-28-27(39)35(19-36)22(17-30(28,3)4)21-11-12-24-32(7)15-14-25(37)31(5,6)23(32)13-16-33(24,8)34(21,9)18-26(35)38/h10-11,22-28,36-39H,12-19H2,1-9H3/b20-10-/t22-,23-,24+,25-,26+,27-,28-,32-,33+,34+,35-/m0/s1
SMILES:	C/C=C(C(=O)O[C@H]1[C@H](O)[C@]2(CO)[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H](C3(C)C)O)[C@@H]2CC1(C)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450240
PubChem CID:	21633166
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
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422131]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	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
ED50	1
IC50	2

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[565738]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1700.0	nM	PMID[565739]
NPT27	Others	Unspecified		IC50	=	5900.0	nM	PMID[565739]

☑ 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 NPC283343 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	230
0.1-0.2	1452
0.2-0.3	4361
0.3-0.4	9569
0.4-0.5	12586
0.5-0.6	6467
0.6-0.7	5097
0.7-0.8	2609
0.8-0.85	269
0.85-0.9	45
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258547
0.9894	High Similarity	NPC473160
0.9789	High Similarity	NPC273668
0.9691	High Similarity	NPC88349
0.9579	High Similarity	NPC474190
0.9495	High Similarity	NPC475263
0.9394	High Similarity	NPC473586
0.8889	High Similarity	NPC96784
0.8889	High Similarity	NPC235920
0.8868	High Similarity	NPC268954
0.8788	High Similarity	NPC476195
0.8774	High Similarity	NPC110861
0.8713	High Similarity	NPC476889
0.8704	High Similarity	NPC470515
0.87	High Similarity	NPC476132
0.8692	High Similarity	NPC44170
0.8687	High Similarity	NPC477875
0.8687	High Similarity	NPC477876
0.8673	High Similarity	NPC88009
0.8673	High Similarity	NPC230151
0.866	High Similarity	NPC215700
0.8624	High Similarity	NPC470914
0.8624	High Similarity	NPC470915
0.8624	High Similarity	NPC470517
0.8624	High Similarity	NPC470911
0.8614	High Similarity	NPC476890
0.8614	High Similarity	NPC40918
0.86	High Similarity	NPC473510
0.86	High Similarity	NPC230546
0.8586	High Similarity	NPC210337
0.8515	High Similarity	NPC93744
0.8515	High Similarity	NPC476888
0.8515	High Similarity	NPC233012
0.8515	High Similarity	NPC54909
0.8511	High Similarity	NPC84121
0.8511	High Similarity	NPC137306
0.8505	High Similarity	NPC473159
0.85	High Similarity	NPC247233
0.8469	Intermediate Similarity	NPC299996
0.8469	Intermediate Similarity	NPC20235
0.8469	Intermediate Similarity	NPC88116
0.8469	Intermediate Similarity	NPC91010
0.8469	Intermediate Similarity	NPC231063
0.8469	Intermediate Similarity	NPC145667
0.8469	Intermediate Similarity	NPC282395
0.8469	Intermediate Similarity	NPC32407
0.8469	Intermediate Similarity	NPC263548
0.8469	Intermediate Similarity	NPC296164
0.8438	Intermediate Similarity	NPC82876
0.8416	Intermediate Similarity	NPC474571
0.8416	Intermediate Similarity	NPC254567
0.8404	Intermediate Similarity	NPC191965
0.84	Intermediate Similarity	NPC51499
0.8381	Intermediate Similarity	NPC88701
0.8367	Intermediate Similarity	NPC136313
0.8367	Intermediate Similarity	NPC86368
0.8367	Intermediate Similarity	NPC53555
0.8367	Intermediate Similarity	NPC74855
0.8367	Intermediate Similarity	NPC307335
0.8365	Intermediate Similarity	NPC477877
0.835	Intermediate Similarity	NPC474124
0.835	Intermediate Similarity	NPC281378
0.8333	Intermediate Similarity	NPC475617
0.8317	Intermediate Similarity	NPC275086
0.8317	Intermediate Similarity	NPC325229
0.8302	Intermediate Similarity	NPC310546
0.83	Intermediate Similarity	NPC25848
0.83	Intermediate Similarity	NPC201657
0.83	Intermediate Similarity	NPC305464
0.83	Intermediate Similarity	NPC204961
0.83	Intermediate Similarity	NPC73004
0.83	Intermediate Similarity	NPC307282
0.83	Intermediate Similarity	NPC173744
0.83	Intermediate Similarity	NPC19376
0.8288	Intermediate Similarity	NPC77689
0.8288	Intermediate Similarity	NPC473839
0.8288	Intermediate Similarity	NPC211093
0.8288	Intermediate Similarity	NPC473636
0.8286	Intermediate Similarity	NPC301666
0.8283	Intermediate Similarity	NPC74751
0.8273	Intermediate Similarity	NPC473405
0.8265	Intermediate Similarity	NPC235884
0.8265	Intermediate Similarity	NPC300351
0.8265	Intermediate Similarity	NPC52021
0.8265	Intermediate Similarity	NPC306541
0.8265	Intermediate Similarity	NPC71074
0.8265	Intermediate Similarity	NPC25299
0.8265	Intermediate Similarity	NPC84319
0.8265	Intermediate Similarity	NPC472149
0.8252	Intermediate Similarity	NPC475344
0.8252	Intermediate Similarity	NPC472552
0.8252	Intermediate Similarity	NPC476471
0.8235	Intermediate Similarity	NPC38855
0.8218	Intermediate Similarity	NPC9613
0.8218	Intermediate Similarity	NPC26413
0.8218	Intermediate Similarity	NPC255589
0.8218	Intermediate Similarity	NPC247139
0.8218	Intermediate Similarity	NPC73911
0.8218	Intermediate Similarity	NPC259788
0.8218	Intermediate Similarity	NPC106112
0.8218	Intermediate Similarity	NPC261935
0.8208	Intermediate Similarity	NPC473483
0.82	Intermediate Similarity	NPC32118
0.82	Intermediate Similarity	NPC96916
0.8198	Intermediate Similarity	NPC471548
0.8191	Intermediate Similarity	NPC253402
0.8191	Intermediate Similarity	NPC159168
0.8182	Intermediate Similarity	NPC214756
0.8182	Intermediate Similarity	NPC169343
0.8182	Intermediate Similarity	NPC295643
0.8182	Intermediate Similarity	NPC275809
0.8182	Intermediate Similarity	NPC38232
0.8182	Intermediate Similarity	NPC272075
0.8173	Intermediate Similarity	NPC473124
0.8173	Intermediate Similarity	NPC473123
0.8173	Intermediate Similarity	NPC473523
0.8163	Intermediate Similarity	NPC130278
0.8163	Intermediate Similarity	NPC120840
0.8163	Intermediate Similarity	NPC78973
0.8163	Intermediate Similarity	NPC49320
0.8163	Intermediate Similarity	NPC113989
0.8155	Intermediate Similarity	NPC11974
0.8155	Intermediate Similarity	NPC235142
0.8155	Intermediate Similarity	NPC472554
0.8137	Intermediate Similarity	NPC471966
0.8137	Intermediate Similarity	NPC159763
0.8137	Intermediate Similarity	NPC271614
0.8137	Intermediate Similarity	NPC111214
0.8137	Intermediate Similarity	NPC92275
0.8137	Intermediate Similarity	NPC29765
0.8137	Intermediate Similarity	NPC124512
0.8137	Intermediate Similarity	NPC278386
0.8131	Intermediate Similarity	NPC475586
0.8131	Intermediate Similarity	NPC127853
0.8125	Intermediate Similarity	NPC131813
0.8125	Intermediate Similarity	NPC475069
0.8125	Intermediate Similarity	NPC175145
0.8119	Intermediate Similarity	NPC158371
0.8119	Intermediate Similarity	NPC473158
0.8119	Intermediate Similarity	NPC98874
0.8119	Intermediate Similarity	NPC473153
0.8119	Intermediate Similarity	NPC259733
0.8119	Intermediate Similarity	NPC327179
0.8119	Intermediate Similarity	NPC207922
0.8113	Intermediate Similarity	NPC283849
0.8113	Intermediate Similarity	NPC471205
0.8113	Intermediate Similarity	NPC475570
0.8108	Intermediate Similarity	NPC473968
0.8108	Intermediate Similarity	NPC475809
0.8108	Intermediate Similarity	NPC134430
0.8105	Intermediate Similarity	NPC238992
0.8103	Intermediate Similarity	NPC470516
0.81	Intermediate Similarity	NPC87095
0.81	Intermediate Similarity	NPC184006
0.81	Intermediate Similarity	NPC23621
0.81	Intermediate Similarity	NPC78580
0.8095	Intermediate Similarity	NPC173583
0.8095	Intermediate Similarity	NPC473127
0.8095	Intermediate Similarity	NPC473543
0.8095	Intermediate Similarity	NPC203354
0.8095	Intermediate Similarity	NPC110656
0.8085	Intermediate Similarity	NPC304285
0.8085	Intermediate Similarity	NPC47763
0.8085	Intermediate Similarity	NPC286786
0.8081	Intermediate Similarity	NPC65120
0.8081	Intermediate Similarity	NPC41239
0.8081	Intermediate Similarity	NPC60755
0.8081	Intermediate Similarity	NPC470590
0.8081	Intermediate Similarity	NPC329842
0.8081	Intermediate Similarity	NPC158030
0.8081	Intermediate Similarity	NPC285184
0.8081	Intermediate Similarity	NPC233455
0.8081	Intermediate Similarity	NPC145067
0.8081	Intermediate Similarity	NPC77099
0.8081	Intermediate Similarity	NPC72845
0.8081	Intermediate Similarity	NPC4036
0.8073	Intermediate Similarity	NPC473125
0.8073	Intermediate Similarity	NPC471967
0.8073	Intermediate Similarity	NPC470063
0.8061	Intermediate Similarity	NPC290972
0.8061	Intermediate Similarity	NPC30522
0.8061	Intermediate Similarity	NPC61543
0.8061	Intermediate Similarity	NPC225585
0.8061	Intermediate Similarity	NPC293048
0.8061	Intermediate Similarity	NPC64872
0.8061	Intermediate Similarity	NPC25906
0.8061	Intermediate Similarity	NPC259875
0.8061	Intermediate Similarity	NPC127689
0.8061	Intermediate Similarity	NPC187785
0.8061	Intermediate Similarity	NPC59263
0.8061	Intermediate Similarity	NPC121798
0.8061	Intermediate Similarity	NPC263393
0.8061	Intermediate Similarity	NPC270768
0.8061	Intermediate Similarity	NPC130520
0.8061	Intermediate Similarity	NPC234346
0.8058	Intermediate Similarity	NPC35239
0.8056	Intermediate Similarity	NPC177047
0.8056	Intermediate Similarity	NPC199457
0.8056	Intermediate Similarity	NPC102914
0.8056	Intermediate Similarity	NPC75747

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 NPC283343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1629
0.2-0.3	3805
0.3-0.4	2335
0.4-0.5	748
0.5-0.6	251
0.6-0.7	147
0.7-0.8	31
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8283	Intermediate Similarity	NPD7748	Approved
0.8218	Intermediate Similarity	NPD7902	Approved
0.8137	Intermediate Similarity	NPD4225	Approved
0.8081	Intermediate Similarity	NPD7515	Phase 2
0.7961	Intermediate Similarity	NPD7638	Approved
0.7921	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7900	Approved
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7766	Intermediate Similarity	NPD7645	Phase 2
0.7739	Intermediate Similarity	NPD8377	Approved
0.7739	Intermediate Similarity	NPD8294	Approved
0.7672	Intermediate Similarity	NPD8033	Approved
0.7672	Intermediate Similarity	NPD8296	Approved
0.7672	Intermediate Similarity	NPD8380	Approved
0.7672	Intermediate Similarity	NPD8335	Approved
0.7672	Intermediate Similarity	NPD8379	Approved
0.7672	Intermediate Similarity	NPD8378	Approved
0.7652	Intermediate Similarity	NPD7516	Approved
0.7636	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7327	Approved
0.7565	Intermediate Similarity	NPD7328	Approved
0.7545	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD7503	Approved
0.7477	Intermediate Similarity	NPD5344	Discontinued
0.7434	Intermediate Similarity	NPD8297	Approved
0.7395	Intermediate Similarity	NPD8328	Phase 3
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7507	Approved
0.7257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7632	Discontinued
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7207	Intermediate Similarity	NPD6675	Approved
0.7207	Intermediate Similarity	NPD6402	Approved
0.7207	Intermediate Similarity	NPD7128	Approved
0.7207	Intermediate Similarity	NPD5739	Approved
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD5697	Approved
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD7319	Approved
0.708	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD8133	Approved
0.7064	Intermediate Similarity	NPD6648	Approved
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD6617	Approved
0.7043	Intermediate Similarity	NPD6649	Approved
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6650	Approved
0.7034	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD6013	Approved
0.7018	Intermediate Similarity	NPD6372	Approved
0.7018	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5701	Approved
0.6991	Remote Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6882	Approved
0.6981	Remote Similarity	NPD6399	Phase 3
0.697	Remote Similarity	NPD7525	Registered
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4632	Approved
0.6893	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD6079	Approved
0.6881	Remote Similarity	NPD6083	Phase 2
0.6881	Remote Similarity	NPD6084	Phase 2
0.688	Remote Similarity	NPD7736	Approved
0.686	Remote Similarity	NPD6319	Approved
0.6857	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD5328	Approved
0.6827	Remote Similarity	NPD3573	Approved
0.6796	Remote Similarity	NPD1694	Approved
0.6792	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD4696	Approved
0.6757	Remote Similarity	NPD5285	Approved
0.6757	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7146	Approved
0.6731	Remote Similarity	NPD5330	Approved
0.6731	Remote Similarity	NPD7334	Approved
0.6731	Remote Similarity	NPD6409	Approved
0.6731	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD6684	Approved
0.6727	Remote Similarity	NPD4755	Approved
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.664	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD5224	Approved
0.6637	Remote Similarity	NPD5226	Approved
0.6637	Remote Similarity	NPD5225	Approved
0.6637	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD5222	Approved
0.6636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD4700	Approved
0.6604	Remote Similarity	NPD6672	Approved
0.6604	Remote Similarity	NPD6903	Approved
0.6604	Remote Similarity	NPD5737	Approved
0.6587	Remote Similarity	NPD6616	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6579	Remote Similarity	NPD5175	Approved
0.6579	Remote Similarity	NPD5174	Approved
0.6577	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD6411	Approved
0.656	Remote Similarity	NPD7604	Phase 2
0.6557	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD4159	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6538	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD8293	Discontinued
0.6535	Remote Similarity	NPD7078	Approved
0.6532	Remote Similarity	NPD8516	Approved
0.6532	Remote Similarity	NPD5983	Phase 2
0.6532	Remote Similarity	NPD8517	Approved
0.6532	Remote Similarity	NPD8515	Approved
0.6532	Remote Similarity	NPD8513	Phase 3
0.6529	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5696	Approved
0.6509	Remote Similarity	NPD7524	Approved
0.6505	Remote Similarity	NPD3667	Approved
0.6486	Remote Similarity	NPD7614	Phase 1
0.6486	Remote Similarity	NPD7732	Phase 3
0.6486	Remote Similarity	NPD4697	Phase 3
0.648	Remote Similarity	NPD6370	Approved
0.6475	Remote Similarity	NPD6317	Approved
0.6465	Remote Similarity	NPD6942	Approved
0.6465	Remote Similarity	NPD7339	Approved
0.6457	Remote Similarity	NPD6336	Discontinued
0.6452	Remote Similarity	NPD6059	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6422	Remote Similarity	NPD7637	Suspended
0.6422	Remote Similarity	NPD5693	Phase 1
0.6417	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6909	Approved
0.64	Remote Similarity	NPD6908	Approved
0.64	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD6015	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4753	Phase 2
0.6389	Remote Similarity	NPD6101	Approved
0.6389	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6356	Remote Similarity	NPD4730	Approved
0.6356	Remote Similarity	NPD4729	Approved
0.6356	Remote Similarity	NPD5128	Approved
0.6349	Remote Similarity	NPD5988	Approved
0.6333	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4768	Approved
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD6008	Approved
0.6311	Remote Similarity	NPD4695	Discontinued
0.63	Remote Similarity	NPD8264	Approved
0.6293	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD8166	Discontinued
0.6286	Remote Similarity	NPD7625	Phase 1
0.6271	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6921	Approved
0.6262	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD6904	Approved
0.6239	Remote Similarity	NPD6673	Approved
0.6239	Remote Similarity	NPD6080	Approved
0.6228	Remote Similarity	NPD5290	Discontinued

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