NPASS Compound

Structure

NPC473526 OpenBabel07101718182D 41 47 0 0 1 0 0 0 0 0999 V2000 3.0578 -2.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7315 1.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1162 4.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2474 -0.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6965 -0.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5482 0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1104 -0.8550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3773 -0.1748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7790 -1.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6240 2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0904 0.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6168 -2.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6894 -1.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7346 -1.5471 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9314 1.3231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2984 3.6664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0242 1.6179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1894 0.8486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7640 -0.2524 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3129 -0.5602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5704 2.0948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2403 -2.1766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6806 -2.6071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 0.3232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2884 0.4147 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3102 -0.7293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2491 -0.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5554 1.0949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0659 -0.5602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6894 -1.3420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5998 0.8001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3911 4.0867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1894 1.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8460 -3.1580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3101 -0.7144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 0.1200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3881 2.6704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7104 0.0708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2043 -1.9106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7255 -1.6081 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 14 1 0 0 0 0 3 16 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 29 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 26 1 0 0 0 0 15 2 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 32 2 0 0 0 0 16 37 1 0 0 0 0 17 31 1 6 0 0 0 18 25 1 0 0 0 0 18 33 1 1 0 0 0 19 24 1 0 0 0 0 19 38 1 0 0 0 0 20 27 1 0 0 0 0 20 30 1 6 0 0 0 21 28 1 1 0 0 0 21 37 1 0 0 0 0 22 30 1 1 0 0 0 22 39 1 0 0 0 0 23 34 2 0 0 0 0 23 40 1 0 0 0 0 24 41 1 1 0 0 0 25 28 1 1 0 0 0 25 29 1 0 0 0 0 26 35 2 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 28 31 1 6 0 0 0 29 36 1 1 0 0 0 30 13 1 6 0 0 0 30 40 1 0 0 0 0 31 8 1 1 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.29
Volume:	564.83
LogP:	2.812
LogD:	1.847
LogS:	-4.408
# Rotatable Bonds:	3
TPSA:	137.82
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	6.661
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
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:	-5.307
MDCK Permeability:	9.323832637164742e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.934
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	32.21229553222656%
Volume Distribution (VD):	0.773
Pgp-substrate:	41.85959243774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.421
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	6.486
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.841
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.745
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.316
Carcinogencity:	0.179
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473526

Natural Product ID:	NPC473526
*Common Name:**	Kadcoccilactone I
IUPAC Name:	n.a.
Synonyms:	Kadcoccilactone I
Standard InCHIKey:	QWSVMFDDOBRKPA-JGLPIVIXSA-N
Standard InCHI:	InChI=1S/C31H44O10/c1-14-9-19(38-26(14)35)24-15(2)17-10-21(37-16(3)32)28(6)25-18(33)11-20-27(4,5)39-22-12-23(34)40-30(20,22)13-29(25,36)7-8-31(17,28)41-24/h14-15,17-22,24-25,33,36H,7-13H2,1-6H3/t14?,15-,17+,18+,19?,20-,21-,22+,24-,25-,28+,29-,30+,31-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@]3([C@@]1(C)[C@@H]1[C@H](O)C[C@@H]4[C@@]5(C[C@@]1(O)CC3)OC(=O)C[C@H]5OC4(C)C)O[C@@H]([C@H]2C)C1CC(C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444702
PubChem CID:	44567836
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[470577]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[470577]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[470577]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[470577]

☑ 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 NPC473526 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	616
0.1-0.2	4445
0.2-0.3	11447
0.3-0.4	12618
0.4-0.5	7499
0.5-0.6	5106
0.6-0.7	843
0.7-0.8	110
0.8-0.85	9
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473701
0.8469	Intermediate Similarity	NPC474065
0.8447	Intermediate Similarity	NPC244969
0.8447	Intermediate Similarity	NPC213528
0.8381	Intermediate Similarity	NPC166079
0.8381	Intermediate Similarity	NPC306776
0.83	Intermediate Similarity	NPC470424
0.8286	Intermediate Similarity	NPC100078
0.8163	Intermediate Similarity	NPC471221
0.8155	Intermediate Similarity	NPC253995
0.8137	Intermediate Similarity	NPC116683
0.8131	Intermediate Similarity	NPC176756
0.8108	Intermediate Similarity	NPC470116
0.8108	Intermediate Similarity	NPC470115
0.8056	Intermediate Similarity	NPC167044
0.8037	Intermediate Similarity	NPC168890
0.802	Intermediate Similarity	NPC476189
0.7982	Intermediate Similarity	NPC217041
0.7981	Intermediate Similarity	NPC211087
0.7959	Intermediate Similarity	NPC476717
0.7909	Intermediate Similarity	NPC475463
0.7909	Intermediate Similarity	NPC182185
0.789	Intermediate Similarity	NPC220773
0.789	Intermediate Similarity	NPC278693
0.7876	Intermediate Similarity	NPC475490
0.785	Intermediate Similarity	NPC471253
0.785	Intermediate Similarity	NPC473406
0.7835	Intermediate Similarity	NPC157328
0.783	Intermediate Similarity	NPC298266
0.783	Intermediate Similarity	NPC259654
0.7798	Intermediate Similarity	NPC469788
0.7798	Intermediate Similarity	NPC469787
0.7798	Intermediate Similarity	NPC290247
0.7788	Intermediate Similarity	NPC79193
0.7778	Intermediate Similarity	NPC154962
0.7778	Intermediate Similarity	NPC177518
0.7778	Intermediate Similarity	NPC169089
0.7778	Intermediate Similarity	NPC88890
0.7778	Intermediate Similarity	NPC123070
0.7778	Intermediate Similarity	NPC18433
0.7778	Intermediate Similarity	NPC18044
0.7778	Intermediate Similarity	NPC132304
0.7778	Intermediate Similarity	NPC114365
0.7768	Intermediate Similarity	NPC98870
0.7757	Intermediate Similarity	NPC470172
0.7755	Intermediate Similarity	NPC65133
0.7755	Intermediate Similarity	NPC291310
0.7723	Intermediate Similarity	NPC477443
0.7723	Intermediate Similarity	NPC477440
0.7712	Intermediate Similarity	NPC129992
0.7706	Intermediate Similarity	NPC228311
0.7706	Intermediate Similarity	NPC41674
0.7706	Intermediate Similarity	NPC469441
0.767	Intermediate Similarity	NPC472238
0.767	Intermediate Similarity	NPC472237
0.7653	Intermediate Similarity	NPC2572
0.7653	Intermediate Similarity	NPC29342
0.7647	Intermediate Similarity	NPC477433
0.7647	Intermediate Similarity	NPC477444
0.7647	Intermediate Similarity	NPC477442
0.7624	Intermediate Similarity	NPC476435
0.7615	Intermediate Similarity	NPC88469
0.76	Intermediate Similarity	NPC64862
0.7593	Intermediate Similarity	NPC471254
0.7593	Intermediate Similarity	NPC292803
0.7576	Intermediate Similarity	NPC477434
0.7568	Intermediate Similarity	NPC329876
0.7549	Intermediate Similarity	NPC61688
0.7549	Intermediate Similarity	NPC200580
0.7547	Intermediate Similarity	NPC328180
0.7547	Intermediate Similarity	NPC278028
0.7547	Intermediate Similarity	NPC471241
0.7525	Intermediate Similarity	NPC239938
0.7524	Intermediate Similarity	NPC21897
0.7524	Intermediate Similarity	NPC62407
0.7524	Intermediate Similarity	NPC287354
0.75	Intermediate Similarity	NPC473350
0.75	Intermediate Similarity	NPC476715
0.75	Intermediate Similarity	NPC178853
0.7477	Intermediate Similarity	NPC274695
0.7477	Intermediate Similarity	NPC292775
0.7476	Intermediate Similarity	NPC470114
0.7455	Intermediate Similarity	NPC470167
0.7453	Intermediate Similarity	NPC475765
0.7453	Intermediate Similarity	NPC476728
0.7453	Intermediate Similarity	NPC193785
0.7451	Intermediate Similarity	NPC477614
0.7451	Intermediate Similarity	NPC226491
0.7429	Intermediate Similarity	NPC329713
0.7429	Intermediate Similarity	NPC477495
0.7429	Intermediate Similarity	NPC76136
0.7429	Intermediate Similarity	NPC217567
0.7426	Intermediate Similarity	NPC472272
0.7407	Intermediate Similarity	NPC108371
0.7404	Intermediate Similarity	NPC52756
0.7404	Intermediate Similarity	NPC216137
0.7398	Intermediate Similarity	NPC475371
0.7368	Intermediate Similarity	NPC469824
0.7368	Intermediate Similarity	NPC473062
0.7364	Intermediate Similarity	NPC469350
0.7358	Intermediate Similarity	NPC17336
0.735	Intermediate Similarity	NPC179429
0.735	Intermediate Similarity	NPC475238
0.7347	Intermediate Similarity	NPC134227
0.7339	Intermediate Similarity	NPC162024
0.7333	Intermediate Similarity	NPC256104
0.7333	Intermediate Similarity	NPC35164
0.7333	Intermediate Similarity	NPC211845
0.7333	Intermediate Similarity	NPC472232
0.7333	Intermediate Similarity	NPC122083
0.7333	Intermediate Similarity	NPC472231
0.7333	Intermediate Similarity	NPC182740
0.7327	Intermediate Similarity	NPC478111
0.7308	Intermediate Similarity	NPC77756
0.73	Intermediate Similarity	NPC69953
0.73	Intermediate Similarity	NPC476721
0.7297	Intermediate Similarity	NPC327093
0.7297	Intermediate Similarity	NPC469629
0.729	Intermediate Similarity	NPC475785
0.729	Intermediate Similarity	NPC145553
0.7288	Intermediate Similarity	NPC475372
0.7282	Intermediate Similarity	NPC201607
0.7282	Intermediate Similarity	NPC221993
0.7282	Intermediate Similarity	NPC191221
0.7282	Intermediate Similarity	NPC470009
0.7282	Intermediate Similarity	NPC56777
0.7281	Intermediate Similarity	NPC474923
0.7281	Intermediate Similarity	NPC48305
0.7273	Intermediate Similarity	NPC469352
0.7264	Intermediate Similarity	NPC206878
0.7264	Intermediate Similarity	NPC470423
0.7255	Intermediate Similarity	NPC477441
0.7255	Intermediate Similarity	NPC80700
0.7241	Intermediate Similarity	NPC97002
0.7241	Intermediate Similarity	NPC285086
0.7238	Intermediate Similarity	NPC475878
0.7238	Intermediate Similarity	NPC473066
0.7228	Intermediate Similarity	NPC471044
0.7228	Intermediate Similarity	NPC473336
0.7227	Intermediate Similarity	NPC312536
0.7222	Intermediate Similarity	NPC472273
0.7222	Intermediate Similarity	NPC253586
0.7217	Intermediate Similarity	NPC472003
0.7212	Intermediate Similarity	NPC67653
0.7212	Intermediate Similarity	NPC471459
0.7212	Intermediate Similarity	NPC56962
0.7212	Intermediate Similarity	NPC24705
0.7203	Intermediate Similarity	NPC473656
0.72	Intermediate Similarity	NPC311642
0.72	Intermediate Similarity	NPC102156
0.72	Intermediate Similarity	NPC242771
0.72	Intermediate Similarity	NPC148740
0.72	Intermediate Similarity	NPC212340
0.72	Intermediate Similarity	NPC164289
0.72	Intermediate Similarity	NPC100366
0.7182	Intermediate Similarity	NPC39683
0.7179	Intermediate Similarity	NPC300051
0.7172	Intermediate Similarity	NPC474714
0.717	Intermediate Similarity	NPC161035
0.7157	Intermediate Similarity	NPC477445
0.7156	Intermediate Similarity	NPC472144
0.7155	Intermediate Similarity	NPC477489
0.7143	Intermediate Similarity	NPC42206
0.713	Intermediate Similarity	NPC98633
0.713	Intermediate Similarity	NPC235109
0.7129	Intermediate Similarity	NPC15091
0.7105	Intermediate Similarity	NPC469826
0.71	Intermediate Similarity	NPC58631
0.71	Intermediate Similarity	NPC254123
0.7094	Intermediate Similarity	NPC102619
0.7094	Intermediate Similarity	NPC52634
0.7087	Intermediate Similarity	NPC302111
0.7087	Intermediate Similarity	NPC114378
0.7087	Intermediate Similarity	NPC103782
0.7087	Intermediate Similarity	NPC215968
0.7087	Intermediate Similarity	NPC155531
0.7087	Intermediate Similarity	NPC477283
0.708	Intermediate Similarity	NPC215408
0.708	Intermediate Similarity	NPC200957
0.708	Intermediate Similarity	NPC295366
0.708	Intermediate Similarity	NPC138908
0.708	Intermediate Similarity	NPC37600
0.7069	Intermediate Similarity	NPC94650
0.7069	Intermediate Similarity	NPC471251
0.7064	Intermediate Similarity	NPC472145
0.7064	Intermediate Similarity	NPC266417
0.7059	Intermediate Similarity	NPC473299
0.7059	Intermediate Similarity	NPC475323
0.7059	Intermediate Similarity	NPC50438
0.7054	Intermediate Similarity	NPC107385
0.7054	Intermediate Similarity	NPC87927
0.7054	Intermediate Similarity	NPC122811
0.7041	Intermediate Similarity	NPC307865
0.7037	Intermediate Similarity	NPC82633
0.7037	Intermediate Similarity	NPC470031
0.7037	Intermediate Similarity	NPC470191
0.7037	Intermediate Similarity	NPC215570
0.7037	Intermediate Similarity	NPC305808
0.7034	Intermediate Similarity	NPC123117
0.7034	Intermediate Similarity	NPC471382

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 NPC473526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	713
0.1-0.2	4339
0.2-0.3	2889
0.3-0.4	716
0.4-0.5	303
0.5-0.6	172
0.6-0.7	15
0.7-0.8	3
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
0.835	Intermediate Similarity	NPD1700	Approved
0.7778	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6697	Approved
0.68	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD6118	Approved
0.67	Remote Similarity	NPD6116	Phase 1
0.6693	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6614	Remote Similarity	NPD6616	Approved
0.6613	Remote Similarity	NPD6059	Approved
0.6613	Remote Similarity	NPD6054	Approved
0.6613	Remote Similarity	NPD6319	Approved
0.66	Remote Similarity	NPD6117	Approved
0.6562	Remote Similarity	NPD8293	Discontinued
0.6512	Remote Similarity	NPD7736	Approved
0.6508	Remote Similarity	NPD6370	Approved
0.65	Remote Similarity	NPD3702	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6462	Remote Similarity	NPD7319	Approved
0.6446	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD6016	Approved
0.6429	Remote Similarity	NPD6015	Approved
0.64	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD229	Approved
0.6387	Remote Similarity	NPD7320	Approved
0.6378	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6357	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD6675	Approved
0.6356	Remote Similarity	NPD7128	Approved
0.6356	Remote Similarity	NPD6402	Approved
0.6356	Remote Similarity	NPD5739	Approved
0.6337	Remote Similarity	NPD3703	Phase 2
0.626	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD8171	Discontinued
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.619	Remote Similarity	NPD6928	Phase 2
0.6179	Remote Similarity	NPD6882	Approved
0.6172	Remote Similarity	NPD6921	Approved
0.6167	Remote Similarity	NPD5697	Approved
0.6167	Remote Similarity	NPD5701	Approved
0.6161	Remote Similarity	NPD8035	Phase 2
0.6161	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD4238	Approved
0.6154	Remote Similarity	NPD4802	Phase 2
0.6148	Remote Similarity	NPD7102	Approved
0.6148	Remote Similarity	NPD6883	Approved
0.6148	Remote Similarity	NPD7290	Approved
0.6136	Remote Similarity	NPD6033	Approved
0.6129	Remote Similarity	NPD8133	Approved
0.6111	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6009	Approved
0.6098	Remote Similarity	NPD6617	Approved
0.6098	Remote Similarity	NPD8130	Phase 1
0.6098	Remote Similarity	NPD6847	Approved
0.6098	Remote Similarity	NPD6869	Approved
0.6082	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7604	Phase 2
0.6066	Remote Similarity	NPD6013	Approved
0.6066	Remote Similarity	NPD6014	Approved
0.6066	Remote Similarity	NPD6012	Approved
0.6048	Remote Similarity	NPD6053	Discontinued
0.6047	Remote Similarity	NPD5983	Phase 2
0.604	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5777	Approved
0.604	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3669	Approved
0.6016	Remote Similarity	NPD4634	Approved
0.6016	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD6011	Approved
0.5981	Remote Similarity	NPD1780	Approved
0.5981	Remote Similarity	NPD1779	Approved
0.5968	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4245	Approved
0.5941	Remote Similarity	NPD4244	Approved
0.5938	Remote Similarity	NPD7327	Approved
0.5938	Remote Similarity	NPD7328	Approved
0.5935	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4755	Approved
0.5891	Remote Similarity	NPD7516	Approved
0.5887	Remote Similarity	NPD6371	Approved
0.5859	Remote Similarity	NPD7115	Discovery
0.5847	Remote Similarity	NPD7638	Approved
0.5842	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3698	Phase 2
0.5833	Remote Similarity	NPD8328	Phase 3
0.5826	Remote Similarity	NPD6399	Phase 3
0.5802	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD8033	Approved
0.5798	Remote Similarity	NPD7639	Approved
0.5798	Remote Similarity	NPD4700	Approved
0.5798	Remote Similarity	NPD7640	Approved
0.5798	Remote Similarity	NPD5286	Approved
0.5798	Remote Similarity	NPD4696	Approved
0.5798	Remote Similarity	NPD5285	Approved
0.5784	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6274	Approved
0.5781	Remote Similarity	NPD6940	Discontinued
0.578	Remote Similarity	NPD6435	Approved
0.5772	Remote Similarity	NPD6412	Phase 2
0.5772	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7101	Approved
0.5769	Remote Similarity	NPD7100	Approved
0.5763	Remote Similarity	NPD6083	Phase 2
0.5763	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5360	Phase 3
0.5729	Remote Similarity	NPD3198	Approved
0.5728	Remote Similarity	NPD6081	Approved
0.5726	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD8294	Approved
0.5725	Remote Similarity	NPD8377	Approved
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD5211	Phase 2
0.5702	Remote Similarity	NPD5226	Approved
0.5702	Remote Similarity	NPD7632	Discontinued
0.5702	Remote Similarity	NPD5225	Approved
0.5692	Remote Similarity	NPD6335	Approved
0.5691	Remote Similarity	NPD4768	Approved
0.5691	Remote Similarity	NPD4767	Approved
0.5682	Remote Similarity	NPD8378	Approved
0.5682	Remote Similarity	NPD6909	Approved
0.5682	Remote Similarity	NPD8335	Approved
0.5682	Remote Similarity	NPD8296	Approved
0.5682	Remote Similarity	NPD8380	Approved
0.5682	Remote Similarity	NPD8379	Approved
0.5682	Remote Similarity	NPD6908	Approved
0.5667	Remote Similarity	NPD8418	Phase 2
0.5656	Remote Similarity	NPD5175	Approved
0.5656	Remote Similarity	NPD5174	Approved
0.5631	Remote Similarity	NPD4789	Approved
0.562	Remote Similarity	NPD5223	Approved
0.5615	Remote Similarity	NPD6317	Approved
0.561	Remote Similarity	NPD5141	Approved
0.56	Remote Similarity	NPD4729	Approved
0.56	Remote Similarity	NPD4730	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