NPASS Compound

Structure

CID170668 OpenBabel06191715542D 52 55 0 0 1 0 0 0 0 0999 V2000 -3.6988 -1.8437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0684 -4.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1661 1.1418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5751 -4.6087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5416 -5.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3401 -5.7214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8682 0.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9026 -3.1062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0831 0.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6331 -0.5861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7026 -4.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7026 -3.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 -4.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 -2.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0603 -4.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2315 -1.0059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7517 -1.7986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1585 -3.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5452 0.4252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3253 -3.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9555 -4.6006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9056 -4.8787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3809 -0.6844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2049 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0603 -3.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2717 -2.2027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3481 0.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1585 -2.5383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7217 -2.9751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0895 -3.1480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7758 -2.4937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9439 -0.0901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9993 -1.5723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2392 -2.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6892 -0.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3168 -1.2556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8428 -0.4345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9926 -3.0204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9216 -4.8705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4182 -4.0810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3280 -0.6393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7000 -2.7474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6582 1.4934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2392 -2.0196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6159 -0.9834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4083 -3.4530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3079 -3.7204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9585 -4.8335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9464 -1.5272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4180 -3.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4120 -1.5389 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 2 18 2 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 35 1 0 0 0 0 10 35 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 36 1 0 0 0 0 17 1 1 1 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 19 37 1 6 0 0 0 20 38 2 0 0 0 0 20 46 1 0 0 0 0 21 39 2 0 0 0 0 21 47 1 0 0 0 0 22 40 2 0 0 0 0 22 48 1 0 0 0 0 23 41 2 0 0 0 0 23 49 1 0 0 0 0 24 42 2 0 0 0 0 24 51 1 0 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 26 36 1 1 0 0 0 27 43 2 0 0 0 0 28 46 1 1 0 0 0 29 47 1 6 0 0 0 30 31 1 0 0 0 0 30 48 1 1 0 0 0 31 33 1 0 0 0 0 31 50 1 6 0 0 0 32 27 1 1 0 0 0 32 35 1 0 0 0 0 32 52 1 0 0 0 0 33 35 1 0 0 0 0 33 49 1 6 0 0 0 34 44 2 0 0 0 0 34 50 1 0 0 0 0 36 37 1 6 0 0 0 36 51 1 0 0 0 0 37 45 1 6 0 0 0 37 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	730.28
Volume:	717.134
LogP:	3.115
LogD:	1.574
LogS:	-3.394
# Rotatable Bonds:	13
TPSA:	204.33
# H-Bond Aceptor:	15
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	6.555
Fsp3:	0.595
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:	-5.279
MDCK Permeability:	0.00010890632984228432
Pgp-inhibitor:	1.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.922
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	50.04295349121094%
Volume Distribution (VD):	1.953
Pgp-substrate:	30.260250091552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	3.943
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.223
Carcinogencity:	0.033
Eye Corrosion:	0.005
Eye Irritation:	0.027
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC170668

Natural Product ID:	NPC170668
*Common Name:**	Kansuinin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VKHCUWUNVKZFBM-PNKWBUBPSA-N
Standard InCHI:	InChI=1S/C37H46O15/c1-17-16-36(51-24(8)42)26(28(17)46-20(4)38)29(47-21(5)39)18(2)30(48-22(6)40)31(50-34(44)25-14-12-11-13-15-25)33(49-23(7)41)35(9,10)32-27(43)19(3)37(36,45)52-32/h11-15,17,19,26,28-33,45H,2,16H2,1,3-10H3/t17-,19+,26+,28-,29-,30-,31+,32-,33+,36+,37+/m0/s1
SMILES:	CC(=O)O[C@H]1C(=C)[C@H](OC(=O)C)[C@H]2[C@@H](OC(=O)C)[C@H](C[C@]2(OC(=O)C)[C@@]2(O[C@H](C([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)C)(C)C)C(=O)[C@H]2C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509463
PubChem CID:	11366139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	ED50	=	7.92	ug ml-1	PMID[567796]
NPT886	Cell Line	NIH3T3	Mus musculus	ED50	=	3.28	ug ml-1	PMID[567796]

☑ 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 NPC170668 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	312
0.1-0.2	1057
0.2-0.3	2505
0.3-0.4	5899
0.4-0.5	10946
0.5-0.6	12795
0.6-0.7	8057
0.7-0.8	926
0.8-0.85	60
0.85-0.9	85
0.9-0.95	54
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC45307
0.9635	High Similarity	NPC474303
0.9635	High Similarity	NPC475413
0.9635	High Similarity	NPC473497
0.9416	High Similarity	NPC86772
0.9366	High Similarity	NPC205389
0.9348	High Similarity	NPC325805
0.9348	High Similarity	NPC272523
0.927	High Similarity	NPC475262
0.927	High Similarity	NPC290833
0.927	High Similarity	NPC265459
0.9236	High Similarity	NPC477101
0.9236	High Similarity	NPC25484
0.9236	High Similarity	NPC232583
0.9236	High Similarity	NPC477097
0.9236	High Similarity	NPC477099
0.922	High Similarity	NPC153214
0.9203	High Similarity	NPC285221
0.9203	High Similarity	NPC194769
0.9197	High Similarity	NPC472250
0.913	High Similarity	NPC79699
0.913	High Similarity	NPC200154
0.913	High Similarity	NPC472247
0.9085	High Similarity	NPC477096
0.9085	High Similarity	NPC477094
0.9085	High Similarity	NPC82467
0.9078	High Similarity	NPC187566
0.9051	High Similarity	NPC233860
0.9048	High Similarity	NPC477100
0.9048	High Similarity	NPC477098
0.9007	High Similarity	NPC475660
0.9007	High Similarity	NPC251294
0.8993	High Similarity	NPC270364
0.8986	High Similarity	NPC472248
0.8944	High Similarity	NPC242355
0.8921	High Similarity	NPC28836
0.8913	High Similarity	NPC239358
0.8905	High Similarity	NPC272946
0.8905	High Similarity	NPC475508
0.8897	High Similarity	NPC477095
0.8882	High Similarity	NPC55744
0.8803	High Similarity	NPC276652
0.8786	High Similarity	NPC311492
0.8786	High Similarity	NPC477368
0.8786	High Similarity	NPC153617
0.8777	High Similarity	NPC233692
0.8732	High Similarity	NPC27721
0.8723	High Similarity	NPC477367
0.8723	High Similarity	NPC232888
0.8714	High Similarity	NPC477364
0.8681	High Similarity	NPC473654
0.8675	High Similarity	NPC70344
0.8671	High Similarity	NPC473301
0.8662	High Similarity	NPC202729
0.8652	High Similarity	NPC324898
0.8652	High Similarity	NPC298547
0.8652	High Similarity	NPC134937
0.8652	High Similarity	NPC477359
0.8633	High Similarity	NPC42234
0.8592	High Similarity	NPC279637
0.8592	High Similarity	NPC149401
0.8591	High Similarity	NPC125033
0.8533	High Similarity	NPC51602
0.8511	High Similarity	NPC477360
0.8487	Intermediate Similarity	NPC469456
0.8472	Intermediate Similarity	NPC327511
0.8472	Intermediate Similarity	NPC205305
0.8414	Intermediate Similarity	NPC121268
0.8414	Intermediate Similarity	NPC53361
0.8411	Intermediate Similarity	NPC471103
0.8411	Intermediate Similarity	NPC161955
0.8403	Intermediate Similarity	NPC477358
0.8389	Intermediate Similarity	NPC477737
0.8369	Intermediate Similarity	NPC475671
0.8369	Intermediate Similarity	NPC122504
0.8369	Intermediate Similarity	NPC475452
0.8369	Intermediate Similarity	NPC3450
0.8366	Intermediate Similarity	NPC282239
0.8366	Intermediate Similarity	NPC21410
0.8366	Intermediate Similarity	NPC473670
0.8365	Intermediate Similarity	NPC40138
0.8357	Intermediate Similarity	NPC472707
0.8354	Intermediate Similarity	NPC324769
0.8354	Intermediate Similarity	NPC325732
0.8322	Intermediate Similarity	NPC134131
0.8322	Intermediate Similarity	NPC127857
0.8322	Intermediate Similarity	NPC25043
0.8312	Intermediate Similarity	NPC217091
0.8312	Intermediate Similarity	NPC106895
0.8286	Intermediate Similarity	NPC472706
0.828	Intermediate Similarity	NPC477188
0.828	Intermediate Similarity	NPC477190
0.828	Intermediate Similarity	NPC43304
0.8258	Intermediate Similarity	NPC472393
0.8243	Intermediate Similarity	NPC475135
0.8228	Intermediate Similarity	NPC66193
0.8227	Intermediate Similarity	NPC477370
0.8224	Intermediate Similarity	NPC7095
0.8224	Intermediate Similarity	NPC112216
0.8217	Intermediate Similarity	NPC329997
0.8214	Intermediate Similarity	NPC477363
0.8214	Intermediate Similarity	NPC477366
0.8205	Intermediate Similarity	NPC471102
0.8201	Intermediate Similarity	NPC8990
0.8201	Intermediate Similarity	NPC472704
0.8201	Intermediate Similarity	NPC477362
0.82	Intermediate Similarity	NPC471100
0.82	Intermediate Similarity	NPC471107
0.8194	Intermediate Similarity	NPC11410
0.8188	Intermediate Similarity	NPC191387
0.8188	Intermediate Similarity	NPC131966
0.8188	Intermediate Similarity	NPC95449
0.8176	Intermediate Similarity	NPC471134
0.817	Intermediate Similarity	NPC101043
0.817	Intermediate Similarity	NPC306799
0.8169	Intermediate Similarity	NPC37968
0.8158	Intermediate Similarity	NPC60509
0.8158	Intermediate Similarity	NPC81698
0.8158	Intermediate Similarity	NPC250046
0.8156	Intermediate Similarity	NPC477365
0.8156	Intermediate Similarity	NPC477357
0.8151	Intermediate Similarity	NPC217673
0.8151	Intermediate Similarity	NPC52523
0.8146	Intermediate Similarity	NPC469513
0.8143	Intermediate Similarity	NPC477369
0.8141	Intermediate Similarity	NPC477735
0.8129	Intermediate Similarity	NPC251139
0.8129	Intermediate Similarity	NPC472703
0.8129	Intermediate Similarity	NPC472549
0.8125	Intermediate Similarity	NPC61891
0.8121	Intermediate Similarity	NPC182869
0.8121	Intermediate Similarity	NPC63737
0.8113	Intermediate Similarity	NPC322420
0.8105	Intermediate Similarity	NPC161239
0.8105	Intermediate Similarity	NPC198455
0.8105	Intermediate Similarity	NPC254558
0.8105	Intermediate Similarity	NPC165260
0.8089	Intermediate Similarity	NPC477736
0.8089	Intermediate Similarity	NPC49297
0.8077	Intermediate Similarity	NPC154675
0.8071	Intermediate Similarity	NPC138798
0.8065	Intermediate Similarity	NPC158333
0.8065	Intermediate Similarity	NPC242262
0.8065	Intermediate Similarity	NPC265395
0.8065	Intermediate Similarity	NPC219419
0.8065	Intermediate Similarity	NPC472005
0.8065	Intermediate Similarity	NPC249471
0.8065	Intermediate Similarity	NPC473414
0.8065	Intermediate Similarity	NPC472030
0.8065	Intermediate Similarity	NPC1173
0.8065	Intermediate Similarity	NPC472022
0.8065	Intermediate Similarity	NPC77719
0.8065	Intermediate Similarity	NPC256142
0.8065	Intermediate Similarity	NPC257213
0.8065	Intermediate Similarity	NPC304876
0.8065	Intermediate Similarity	NPC471135
0.8065	Intermediate Similarity	NPC237549
0.8065	Intermediate Similarity	NPC472657
0.8065	Intermediate Similarity	NPC472658
0.8054	Intermediate Similarity	NPC77493
0.8026	Intermediate Similarity	NPC478263
0.8026	Intermediate Similarity	NPC240115
0.8025	Intermediate Similarity	NPC469417
0.8025	Intermediate Similarity	NPC181924
0.8025	Intermediate Similarity	NPC102465
0.8014	Intermediate Similarity	NPC246166
0.8013	Intermediate Similarity	NPC80895
0.8013	Intermediate Similarity	NPC473611
0.8013	Intermediate Similarity	NPC155329
0.8013	Intermediate Similarity	NPC26033
0.8013	Intermediate Similarity	NPC114357
0.8013	Intermediate Similarity	NPC471912
0.8013	Intermediate Similarity	NPC114410
0.8013	Intermediate Similarity	NPC228204
0.8013	Intermediate Similarity	NPC259144
0.8013	Intermediate Similarity	NPC112523
0.8012	Intermediate Similarity	NPC477491
0.8	Intermediate Similarity	NPC192658
0.8	Intermediate Similarity	NPC472548
0.8	Intermediate Similarity	NPC472546
0.8	Intermediate Similarity	NPC150893
0.8	Intermediate Similarity	NPC22571
0.8	Intermediate Similarity	NPC329960
0.8	Intermediate Similarity	NPC477905
0.8	Intermediate Similarity	NPC469647
0.8	Intermediate Similarity	NPC283875
0.8	Intermediate Similarity	NPC469648
0.8	Intermediate Similarity	NPC138641
0.8	Intermediate Similarity	NPC295408
0.7987	Intermediate Similarity	NPC87934
0.7987	Intermediate Similarity	NPC476173
0.7987	Intermediate Similarity	NPC162613
0.7987	Intermediate Similarity	NPC473440
0.7987	Intermediate Similarity	NPC473214
0.7987	Intermediate Similarity	NPC470245
0.7962	Intermediate Similarity	NPC475638
0.7962	Intermediate Similarity	NPC475548
0.7962	Intermediate Similarity	NPC290683
0.7962	Intermediate Similarity	NPC326235
0.7962	Intermediate Similarity	NPC323001

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 NPC170668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	728
0.2-0.3	1854
0.3-0.4	2954
0.4-0.5	2179
0.5-0.6	932
0.6-0.7	233
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD7799	Discontinued
0.8322	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7236	Approved
0.7821	Intermediate Similarity	NPD7239	Suspended
0.7655	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8407	Phase 2
0.7529	Intermediate Similarity	NPD8368	Discontinued
0.7378	Intermediate Similarity	NPD7057	Phase 3
0.7378	Intermediate Similarity	NPD7058	Phase 2
0.7267	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8435	Approved
0.7225	Intermediate Similarity	NPD7685	Pre-registration
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7194	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8361	Approved
0.7135	Intermediate Similarity	NPD8360	Approved
0.7119	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6599	Discontinued
0.7067	Intermediate Similarity	NPD6085	Phase 2
0.7067	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7961	Discontinued
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5761	Phase 2
0.7048	Intermediate Similarity	NPD5760	Phase 2
0.7044	Intermediate Similarity	NPD4628	Phase 3
0.7029	Intermediate Similarity	NPD6764	Approved
0.7029	Intermediate Similarity	NPD6685	Approved
0.7029	Intermediate Similarity	NPD6765	Approved
0.7024	Intermediate Similarity	NPD7075	Discontinued
0.7007	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2067	Discontinued
0.6993	Remote Similarity	NPD2629	Approved
0.6982	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6002	Phase 3
0.6962	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6005	Phase 3
0.6962	Remote Similarity	NPD6004	Phase 3
0.6954	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4198	Discontinued
0.6929	Remote Similarity	NPD2182	Approved
0.6914	Remote Similarity	NPD6799	Approved
0.6901	Remote Similarity	NPD969	Suspended
0.6882	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6785	Approved
0.6872	Remote Similarity	NPD6784	Approved
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5647	Approved
0.6839	Remote Similarity	NPD8462	Phase 1
0.6833	Remote Similarity	NPD8150	Discontinued
0.6812	Remote Similarity	NPD5765	Approved
0.6811	Remote Similarity	NPD8485	Approved
0.6803	Remote Similarity	NPD7741	Discontinued
0.6792	Remote Similarity	NPD7137	Phase 2
0.679	Remote Similarity	NPD6190	Approved
0.6786	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6801	Discontinued
0.6783	Remote Similarity	NPD6912	Phase 3
0.6761	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6355	Discontinued
0.6724	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6653	Approved
0.6706	Remote Similarity	NPD3817	Phase 2
0.6706	Remote Similarity	NPD5402	Approved
0.6691	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9545	Approved
0.6688	Remote Similarity	NPD3661	Approved
0.6688	Remote Similarity	NPD3663	Approved
0.6688	Remote Similarity	NPD3662	Phase 3
0.6688	Remote Similarity	NPD3664	Approved
0.6687	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6647	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD5763	Approved
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD164	Approved
0.6628	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2575	Approved
0.661	Remote Similarity	NPD3818	Discontinued
0.6607	Remote Similarity	NPD7458	Discontinued
0.66	Remote Similarity	NPD5125	Phase 3
0.66	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5126	Approved
0.6575	Remote Similarity	NPD8313	Approved
0.6575	Remote Similarity	NPD8312	Approved
0.6573	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6647	Phase 2
0.6568	Remote Similarity	NPD4380	Phase 2
0.6566	Remote Similarity	NPD2532	Approved
0.6566	Remote Similarity	NPD2534	Approved
0.6566	Remote Similarity	NPD2533	Approved
0.6562	Remote Similarity	NPD8320	Phase 1
0.6562	Remote Similarity	NPD8319	Approved
0.6543	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6273	Approved
0.6524	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7305	Phase 1
0.6519	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7808	Phase 3
0.6514	Remote Similarity	NPD7199	Phase 2
0.6514	Remote Similarity	NPD8127	Discontinued
0.6513	Remote Similarity	NPD6287	Discontinued
0.6513	Remote Similarity	NPD4807	Approved
0.6513	Remote Similarity	NPD7492	Approved
0.6513	Remote Similarity	NPD4806	Approved
0.6507	Remote Similarity	NPD6858	Approved
0.6507	Remote Similarity	NPD7094	Approved
0.6506	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7008	Discontinued
0.6494	Remote Similarity	NPD7736	Approved
0.649	Remote Similarity	NPD5306	Approved
0.649	Remote Similarity	NPD5305	Approved
0.6488	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5048	Discontinued
0.6471	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD7028	Phase 2
0.6467	Remote Similarity	NPD6054	Approved
0.6464	Remote Similarity	NPD7251	Discontinued
0.6452	Remote Similarity	NPD6362	Approved
0.645	Remote Similarity	NPD8404	Phase 2
0.6442	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7078	Approved
0.6425	Remote Similarity	NPD7497	Discontinued
0.6425	Remote Similarity	NPD7435	Discontinued
0.6421	Remote Similarity	NPD7700	Phase 2
0.6421	Remote Similarity	NPD7699	Phase 2
0.642	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD2799	Discontinued
0.6416	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6663	Approved
0.6412	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2798	Approved
0.6409	Remote Similarity	NPD6797	Phase 2
0.6408	Remote Similarity	NPD1237	Approved
0.6403	Remote Similarity	NPD9495	Approved
0.6398	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3887	Approved
0.6386	Remote Similarity	NPD2354	Approved
0.6382	Remote Similarity	NPD6370	Approved
0.6379	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6559	Discontinued
0.637	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5204	Approved
0.6369	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7473	Discontinued
0.6364	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5494	Approved
0.6364	Remote Similarity	NPD2800	Approved
0.6358	Remote Similarity	NPD2569	Approved
0.6358	Remote Similarity	NPD7972	Discontinued
0.6358	Remote Similarity	NPD2567	Approved
0.6358	Remote Similarity	NPD6319	Approved
0.6357	Remote Similarity	NPD1238	Approved
0.6354	Remote Similarity	NPD7074	Phase 3
0.6352	Remote Similarity	NPD2313	Discontinued
0.6351	Remote Similarity	NPD2652	Approved
0.6351	Remote Similarity	NPD2650	Approved
0.6349	Remote Similarity	NPD6534	Approved
0.6349	Remote Similarity	NPD6535	Approved
0.634	Remote Similarity	NPD4135	Approved
0.634	Remote Similarity	NPD4136	Approved
0.634	Remote Similarity	NPD4106	Approved
0.6338	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD1930	Approved
0.6338	Remote Similarity	NPD1929	Approved
0.6337	Remote Similarity	NPD7411	Suspended
0.6333	Remote Similarity	NPD9493	Approved
0.6333	Remote Similarity	NPD3751	Discontinued
0.6329	Remote Similarity	NPD6832	Phase 2
0.6325	Remote Similarity	NPD8166	Discontinued
0.6323	Remote Similarity	NPD8293	Discontinued
0.6319	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3226	Approved
0.6316	Remote Similarity	NPD6016	Approved
0.6316	Remote Similarity	NPD6015	Approved
0.6313	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6166	Phase 2
0.6313	Remote Similarity	NPD7874	Approved
0.6312	Remote Similarity	NPD6233	Phase 2
0.6309	Remote Similarity	NPD5951	Approved
0.6307	Remote Similarity	NPD919	Approved
0.6307	Remote Similarity	NPD6234	Discontinued
0.6303	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6371	Approved
0.6301	Remote Similarity	NPD1934	Approved
0.6298	Remote Similarity	NPD7054	Approved
0.6294	Remote Similarity	NPD920	Approved
0.6292	Remote Similarity	NPD3787	Discontinued
0.6289	Remote Similarity	NPD7095	Approved
0.6286	Remote Similarity	NPD4965	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