NPASS Compound

Structure

CID162613 OpenBabel06191715532D 47 50 0 0 1 0 0 0 0 0999 V2000 -1.6534 1.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4974 1.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3140 2.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7985 -2.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9639 3.4604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7090 -0.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8804 -0.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6241 0.5901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2140 0.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7096 -1.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8769 -2.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7096 -0.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0441 -1.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8769 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5503 -0.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4845 2.7436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 1.0384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6250 1.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 3.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8477 -2.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0050 3.3886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9572 -1.5855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0441 -0.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9016 0.2866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4391 2.6288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5995 -0.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7851 1.2171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3513 0.8951 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7133 0.2582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1295 1.7278 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9188 -0.2834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2114 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2117 1.4587 0.0000 C 0 0 0 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 1.0803 1.8711 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6846 3.8245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4964 -3.2937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5366 4.1830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1005 -2.5363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8524 0.4299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2114 0.7390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5798 2.0047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0931 3.3336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2482 -1.6468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4122 2.5222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0621 -1.2342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3787 -0.7033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 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 33 1 0 0 0 0 8 33 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 23 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 0 0 0 0 16 25 1 0 0 0 0 16 35 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 18 27 2 0 0 0 0 19 36 2 0 0 0 0 19 43 1 0 0 0 0 20 37 2 0 0 0 0 20 44 1 0 0 0 0 21 38 2 0 0 0 0 21 45 1 0 0 0 0 22 39 2 0 0 0 0 22 46 1 0 0 0 0 23 32 1 0 0 0 0 24 40 1 6 0 0 0 25 43 1 6 0 0 0 26 34 1 1 0 0 0 26 44 1 0 0 0 0 27 29 1 0 0 0 0 27 35 1 0 0 0 0 28 30 1 0 0 0 0 28 34 1 1 0 0 0 29 31 1 0 0 0 0 29 47 1 1 0 0 0 30 35 1 6 0 0 0 30 45 1 0 0 0 0 31 34 1 6 0 0 0 31 46 1 0 0 0 0 32 41 2 0 0 0 0 32 47 1 0 0 0 0 33 42 1 0 0 0 0 34 9 1 1 0 0 0 35 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.28
Volume:	658.808
LogP:	2.529
LogD:	2.189
LogS:	-4.423
# Rotatable Bonds:	12
TPSA:	171.96
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	5.133
Fsp3:	0.571
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:	-5.419
MDCK Permeability:	0.00013739046698901802
Pgp-inhibitor:	0.996
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.693
20% Bioavailability (F20%):	0.288
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.335
Plasma Protein Binding (PPB):	52.076087951660156%
Volume Distribution (VD):	1.714
Pgp-substrate:	25.149198532104492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.376
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	3.408
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.109
Carcinogencity:	0.135
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC162613

Natural Product ID:	NPC162613
*Common Name:**	[(2S,4R,5R,5As,6S,8S,9Ar,10S,10As)-2,5,6,10-Tetraacetyloxy-8-Hydroxy-10A-(2-Hydroxypropan-2-Yl)-3,5A-Dimethyl-9-Methylidene-2,4,5,6,7,8,9A,10-Octahydro-1H-Benzo[G]Azulen-4-Yl] Benzoate
IUPAC Name:	[(2S,4R,5R,5aS,6S,8S,9aR,10S,10aS)-2,5,6,10-tetraacetyloxy-8-hydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate
Synonyms:
Standard InCHIKey:	JQCUSGKZTBCFPV-BEISSDHJSA-N
Standard InCHI:	InChI=1S/C35H44O12/c1-17-24(40)15-26(44-20(4)37)34(9)28(17)30(45-21(5)38)35(33(7,8)42)16-25(43-19(3)36)18(2)27(35)29(31(34)46-22(6)39)47-32(41)23-13-11-10-12-14-23/h10-14,24-26,28-31,40,42H,1,15-16H2,2-9H3/t24-,25-,26-,28-,29+,30-,31-,34+,35-/m0/s1
SMILES:	C=C1[C@H](C[C@@H]([C@]2(C)[C@@H]1[C@@H]([C@@]1(C[C@@H](C(=C1[C@H]([C@@H]2OC(=O)C)OC(=O)c1ccccc1)C)OC(=O)C)C(C)(C)O)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL339718
PubChem CID:	5321678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15125.1	Taxus wallichiana var. chinensis	Varieties	Taxaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[450072]
NPT2	Others	Unspecified		Control	=	158.0	%	PMID[450072]
NPT2	Others	Unspecified		Control	=	313.0	%	PMID[450072]
NPT27	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[450072]

☑ 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 NPC162613 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	274
0.1-0.2	985
0.2-0.3	2204
0.3-0.4	4655
0.4-0.5	9081
0.5-0.6	11355
0.6-0.7	12193
0.7-0.8	1611
0.8-0.85	228
0.85-0.9	95
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87934
0.9924	High Similarity	NPC9905
0.985	High Similarity	NPC192658
0.9704	High Similarity	NPC34943
0.9632	High Similarity	NPC125882
0.963	High Similarity	NPC95449
0.9627	High Similarity	NPC266374
0.9562	High Similarity	NPC240115
0.9562	High Similarity	NPC20255
0.9489	High Similarity	NPC92867
0.9489	High Similarity	NPC311825
0.9353	High Similarity	NPC473760
0.9281	High Similarity	NPC209592
0.9281	High Similarity	NPC48599
0.9143	High Similarity	NPC312393
0.9143	High Similarity	NPC473602
0.9085	High Similarity	NPC31829
0.9015	High Similarity	NPC58061
0.8986	High Similarity	NPC472547
0.8986	High Similarity	NPC90614
0.8936	High Similarity	NPC472556
0.8931	High Similarity	NPC284022
0.8921	High Similarity	NPC41481
0.8921	High Similarity	NPC97947
0.8921	High Similarity	NPC118080
0.8921	High Similarity	NPC291599
0.8921	High Similarity	NPC27377
0.8921	High Similarity	NPC16912
0.8921	High Similarity	NPC472576
0.8921	High Similarity	NPC87448
0.8913	High Similarity	NPC473301
0.8905	High Similarity	NPC472372
0.8905	High Similarity	NPC472374
0.8897	High Similarity	NPC28836
0.8857	High Similarity	NPC34012
0.8849	High Similarity	NPC275592
0.8849	High Similarity	NPC171207
0.8849	High Similarity	NPC100913
0.8849	High Similarity	NPC97667
0.8841	High Similarity	NPC39549
0.8828	High Similarity	NPC138641
0.8828	High Similarity	NPC22571
0.8828	High Similarity	NPC469648
0.8828	High Similarity	NPC469647
0.8828	High Similarity	NPC233581
0.8828	High Similarity	NPC283875
0.8828	High Similarity	NPC145649
0.8824	High Similarity	NPC472248
0.8811	High Similarity	NPC132652
0.8811	High Similarity	NPC327031
0.8803	High Similarity	NPC472575
0.8803	High Similarity	NPC70403
0.8803	High Similarity	NPC470159
0.8803	High Similarity	NPC472568
0.8803	High Similarity	NPC469349
0.8803	High Similarity	NPC471104
0.8803	High Similarity	NPC29704
0.8803	High Similarity	NPC174982
0.8803	High Similarity	NPC177940
0.8803	High Similarity	NPC472572
0.8803	High Similarity	NPC473088
0.8803	High Similarity	NPC184817
0.8803	High Similarity	NPC96903
0.8803	High Similarity	NPC171525
0.8803	High Similarity	NPC476973
0.8803	High Similarity	NPC472571
0.8803	High Similarity	NPC470157
0.8803	High Similarity	NPC158663
0.8803	High Similarity	NPC200471
0.8794	High Similarity	NPC163087
0.8794	High Similarity	NPC131966
0.8794	High Similarity	NPC191387
0.8794	High Similarity	NPC477894
0.8786	High Similarity	NPC242355
0.8768	High Similarity	NPC472551
0.8768	High Similarity	NPC472545
0.8768	High Similarity	NPC202729
0.8759	High Similarity	NPC311492
0.875	High Similarity	NPC239358
0.875	High Similarity	NPC233692
0.875	High Similarity	NPC233860
0.8741	High Similarity	NPC478263
0.8732	High Similarity	NPC470152
0.8732	High Similarity	NPC70716
0.8732	High Similarity	NPC241951
0.8732	High Similarity	NPC95265
0.8732	High Similarity	NPC125106
0.8732	High Similarity	NPC95810
0.8732	High Similarity	NPC57628
0.8732	High Similarity	NPC472573
0.8732	High Similarity	NPC25768
0.8732	High Similarity	NPC476974
0.8732	High Similarity	NPC38696
0.8732	High Similarity	NPC472569
0.8732	High Similarity	NPC188865
0.8732	High Similarity	NPC472570
0.8732	High Similarity	NPC475122
0.8732	High Similarity	NPC475759
0.8732	High Similarity	NPC11685
0.8732	High Similarity	NPC163719
0.8723	High Similarity	NPC472546
0.8707	High Similarity	NPC132599
0.8707	High Similarity	NPC473611
0.8707	High Similarity	NPC469730
0.8707	High Similarity	NPC473632
0.8705	High Similarity	NPC27721
0.8696	High Similarity	NPC200154
0.8696	High Similarity	NPC291638
0.8696	High Similarity	NPC472577
0.8696	High Similarity	NPC195647
0.8696	High Similarity	NPC477893
0.8696	High Similarity	NPC66761
0.8696	High Similarity	NPC17877
0.869	High Similarity	NPC476173
0.8671	High Similarity	NPC478264
0.8671	High Similarity	NPC25043
0.8671	High Similarity	NPC134131
0.8662	High Similarity	NPC91703
0.8652	High Similarity	NPC224491
0.8649	High Similarity	NPC11410
0.8639	High Similarity	NPC471135
0.863	High Similarity	NPC470153
0.863	High Similarity	NPC472398
0.8623	High Similarity	NPC298547
0.8623	High Similarity	NPC134937
0.8623	High Similarity	NPC474608
0.8623	High Similarity	NPC324898
0.8621	High Similarity	NPC301556
0.8621	High Similarity	NPC92293
0.8621	High Similarity	NPC270590
0.8621	High Similarity	NPC471101
0.8621	High Similarity	NPC476975
0.8621	High Similarity	NPC76103
0.8621	High Similarity	NPC266265
0.8611	High Similarity	NPC474935
0.8603	High Similarity	NPC147561
0.8592	High Similarity	NPC140021
0.8582	High Similarity	NPC184747
0.8582	High Similarity	NPC4341
0.8582	High Similarity	NPC473085
0.8582	High Similarity	NPC473081
0.8582	High Similarity	NPC473613
0.8582	High Similarity	NPC48017
0.8582	High Similarity	NPC200592
0.8582	High Similarity	NPC147880
0.8582	High Similarity	NPC43241
0.8582	High Similarity	NPC473758
0.8582	High Similarity	NPC211137
0.8582	High Similarity	NPC473109
0.8582	High Similarity	NPC473112
0.8582	High Similarity	NPC473060
0.8582	High Similarity	NPC476094
0.8582	High Similarity	NPC275576
0.8581	High Similarity	NPC251139
0.8571	High Similarity	NPC327511
0.8571	High Similarity	NPC205305
0.8562	High Similarity	NPC473214
0.8562	High Similarity	NPC125033
0.8562	High Similarity	NPC470245
0.8561	High Similarity	NPC477896
0.8561	High Similarity	NPC149401
0.8561	High Similarity	NPC279637
0.8552	High Similarity	NPC281717
0.8533	High Similarity	NPC319404
0.8523	High Similarity	NPC475548
0.8523	High Similarity	NPC290683
0.8523	High Similarity	NPC475638
0.8519	High Similarity	NPC169913
0.8511	High Similarity	NPC53361
0.8511	High Similarity	NPC210591
0.8511	High Similarity	NPC475652
0.8511	High Similarity	NPC121268
0.8511	High Similarity	NPC214550
0.8503	High Similarity	NPC96308
0.8493	Intermediate Similarity	NPC473215
0.8489	Intermediate Similarity	NPC48929
0.8489	Intermediate Similarity	NPC153617
0.8478	Intermediate Similarity	NPC238370
0.8467	Intermediate Similarity	NPC475508
0.8467	Intermediate Similarity	NPC318447
0.8467	Intermediate Similarity	NPC322048
0.8462	Intermediate Similarity	NPC182869
0.8456	Intermediate Similarity	NPC21410
0.8456	Intermediate Similarity	NPC473670
0.8451	Intermediate Similarity	NPC183270
0.8451	Intermediate Similarity	NPC477904
0.8446	Intermediate Similarity	NPC477905
0.8446	Intermediate Similarity	NPC472548
0.844	Intermediate Similarity	NPC183122
0.844	Intermediate Similarity	NPC475373
0.844	Intermediate Similarity	NPC283375
0.8435	Intermediate Similarity	NPC7095
0.8425	Intermediate Similarity	NPC217918
0.8421	Intermediate Similarity	NPC476077
0.8414	Intermediate Similarity	NPC127857
0.8411	Intermediate Similarity	NPC476784
0.8406	Intermediate Similarity	NPC72915
0.8403	Intermediate Similarity	NPC191082
0.8403	Intermediate Similarity	NPC475429
0.8403	Intermediate Similarity	NPC473673

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 NPC162613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	714
0.2-0.3	1489
0.3-0.4	2667
0.4-0.5	2290
0.5-0.6	1296
0.6-0.7	445
0.7-0.8	23
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
0.8041	Intermediate Similarity	NPD7236	Approved
0.7895	Intermediate Similarity	NPD7239	Suspended
0.7857	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7799	Discontinued
0.7692	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD7741	Discontinued
0.7556	Intermediate Similarity	NPD2629	Approved
0.755	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7057	Phase 3
0.7438	Intermediate Similarity	NPD7058	Phase 2
0.7415	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8368	Discontinued
0.7368	Intermediate Similarity	NPD8434	Phase 2
0.7353	Intermediate Similarity	NPD8407	Phase 2
0.7279	Intermediate Similarity	NPD3764	Approved
0.7256	Intermediate Similarity	NPD8127	Discontinued
0.7239	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2182	Approved
0.7211	Intermediate Similarity	NPD7008	Discontinued
0.7197	Intermediate Similarity	NPD6273	Approved
0.7184	Intermediate Similarity	NPD8361	Approved
0.7184	Intermediate Similarity	NPD8360	Approved
0.7122	Intermediate Similarity	NPD4198	Discontinued
0.7121	Intermediate Similarity	NPD6647	Phase 2
0.7114	Intermediate Similarity	NPD7961	Discontinued
0.711	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7819	Suspended
0.709	Intermediate Similarity	NPD6685	Approved
0.7086	Intermediate Similarity	NPD8435	Approved
0.7076	Intermediate Similarity	NPD7685	Pre-registration
0.7069	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6190	Approved
0.7051	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5951	Approved
0.7013	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6004	Phase 3
0.7013	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6005	Phase 3
0.7013	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6663	Approved
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD5760	Phase 2
0.6987	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD8166	Discontinued
0.6972	Remote Similarity	NPD9545	Approved
0.697	Remote Similarity	NPD7075	Discontinued
0.6959	Remote Similarity	NPD5736	Approved
0.6944	Remote Similarity	NPD8485	Approved
0.6944	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.694	Remote Similarity	NPD164	Approved
0.6933	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6599	Discontinued
0.6914	Remote Similarity	NPD4380	Phase 2
0.6909	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD4965	Approved
0.6909	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4966	Approved
0.6908	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD6355	Discontinued
0.6903	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5844	Phase 1
0.6897	Remote Similarity	NPD6287	Discontinued
0.6894	Remote Similarity	NPD1238	Approved
0.6892	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6085	Phase 2
0.689	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6765	Approved
0.6879	Remote Similarity	NPD6764	Approved
0.6879	Remote Similarity	NPD3750	Approved
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD5125	Phase 3
0.6866	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5765	Approved
0.6863	Remote Similarity	NPD6653	Approved
0.6859	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7458	Discontinued
0.6852	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5402	Approved
0.6839	Remote Similarity	NPD2935	Discontinued
0.6835	Remote Similarity	NPD6912	Phase 3
0.6832	Remote Similarity	NPD5403	Approved
0.6831	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6801	Discontinued
0.6816	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1237	Approved
0.6813	Remote Similarity	NPD2533	Approved
0.6813	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2532	Approved
0.6813	Remote Similarity	NPD2534	Approved
0.6812	Remote Similarity	NPD2067	Discontinued
0.6807	Remote Similarity	NPD7768	Phase 2
0.68	Remote Similarity	NPD8312	Approved
0.68	Remote Similarity	NPD8313	Approved
0.6795	Remote Similarity	NPD5763	Approved
0.6795	Remote Similarity	NPD5762	Approved
0.6795	Remote Similarity	NPD7266	Discontinued
0.6786	Remote Similarity	NPD7094	Approved
0.6786	Remote Similarity	NPD6858	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6781	Remote Similarity	NPD4806	Approved
0.6781	Remote Similarity	NPD4807	Approved
0.6774	Remote Similarity	NPD2799	Discontinued
0.6774	Remote Similarity	NPD7305	Phase 1
0.6772	Remote Similarity	NPD7003	Approved
0.6772	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5048	Discontinued
0.6763	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5305	Approved
0.6759	Remote Similarity	NPD5306	Approved
0.675	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1930	Approved
0.6741	Remote Similarity	NPD1929	Approved
0.6741	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7137	Phase 2
0.6726	Remote Similarity	NPD6234	Discontinued
0.6724	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6784	Approved
0.6723	Remote Similarity	NPD6785	Approved
0.6711	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5401	Approved
0.6706	Remote Similarity	NPD6232	Discontinued
0.6691	Remote Similarity	NPD5909	Discontinued
0.6689	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8455	Phase 2
0.6686	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7715	Approved
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD4110	Phase 3
0.6647	Remote Similarity	NPD7228	Approved
0.6647	Remote Similarity	NPD3817	Phase 2
0.6647	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD3818	Discontinued
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3226	Approved
0.6645	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2066	Phase 3
0.6631	Remote Similarity	NPD7497	Discontinued
0.6627	Remote Similarity	NPD1934	Approved
0.6626	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2438	Suspended
0.6624	Remote Similarity	NPD6099	Approved
0.6624	Remote Similarity	NPD6100	Approved
0.6624	Remote Similarity	NPD1551	Phase 2
0.6623	Remote Similarity	NPD4140	Approved
0.6622	Remote Similarity	NPD1608	Approved
0.6609	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2797	Approved
0.6599	Remote Similarity	NPD4135	Approved
0.6599	Remote Similarity	NPD4136	Approved
0.6599	Remote Similarity	NPD4106	Approved
0.6597	Remote Similarity	NPD9493	Approved
0.6587	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2346	Discontinued
0.6571	Remote Similarity	NPD7074	Phase 3
0.6567	Remote Similarity	NPD9495	Approved
0.6562	Remote Similarity	NPD2575	Approved
0.6561	Remote Similarity	NPD4308	Phase 3
0.6561	Remote Similarity	NPD1510	Phase 2
0.6558	Remote Similarity	NPD8032	Phase 2
0.6556	Remote Similarity	NPD5647	Approved
0.6541	Remote Similarity	NPD1549	Phase 2
0.6536	Remote Similarity	NPD7095	Approved
0.6533	Remote Similarity	NPD1876	Approved
0.6532	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6166	Phase 2
0.6532	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5405	Approved
0.6519	Remote Similarity	NPD2796	Approved
0.6519	Remote Similarity	NPD5408	Approved
0.6519	Remote Similarity	NPD7798	Approved
0.6519	Remote Similarity	NPD5404	Approved
0.6519	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5406	Approved
0.6516	Remote Similarity	NPD1240	Approved
0.6514	Remote Similarity	NPD7054	Approved
0.6513	Remote Similarity	NPD5204	Approved
0.651	Remote Similarity	NPD6637	Approved
0.6509	Remote Similarity	NPD3882	Suspended
0.6508	Remote Similarity	NPD8320	Phase 1
0.6508	Remote Similarity	NPD8319	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