NPASS Compound

Structure

NPC38420 OpenBabel07101719132D 43 45 0 0 1 0 0 0 0 0999 V2000 -2.7169 4.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8302 3.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5543 2.9176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1298 -1.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6946 3.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1133 1.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 -2.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5680 -1.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7019 -1.6992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5680 -0.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8359 -1.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7019 0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9718 2.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0321 2.1516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1245 2.9132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4115 1.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1736 0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8905 3.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9115 2.1516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4718 -0.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0715 4.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2870 2.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3473 -1.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8359 -0.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5321 1.2856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5924 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2378 0.3008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1848 3.2552 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7057 0.3008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4718 -0.3420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4187 2.6124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9699 0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9397 -0.3420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1022 5.5668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2267 2.6537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -1.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 -1.2817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9699 1.3008 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 -1.0111 4.2400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 2.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -1.3268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1039 -0.1992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 2 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 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 24 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 15 18 2 0 0 0 0 16 19 2 0 0 0 0 16 27 1 0 0 0 0 17 26 2 0 0 0 0 17 39 1 0 0 0 0 20 30 1 0 0 0 0 21 34 2 0 0 0 0 21 40 1 0 0 0 0 22 35 2 0 0 0 0 22 41 1 0 0 0 0 23 36 2 0 0 0 0 23 42 1 0 0 0 0 24 32 1 0 0 0 0 25 14 1 6 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 27 30 1 0 0 0 0 27 43 1 1 0 0 0 28 15 1 1 0 0 0 28 31 1 0 0 0 0 28 40 1 0 0 0 0 29 20 1 1 0 0 0 29 33 1 0 0 0 0 30 37 1 6 0 0 0 31 41 1 1 0 0 0 32 38 2 0 0 0 0 32 43 1 0 0 0 0 33 39 1 0 0 0 0 33 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.26
Volume:	612.556
LogP:	3.759
LogD:	2.799
LogS:	-3.872
# Rotatable Bonds:	12
TPSA:	134.66
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.451
Fsp3:	0.455
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:	-5.268
MDCK Permeability:	0.00015006109606474638
Pgp-inhibitor:	0.75
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	82.01639556884766%
Volume Distribution (VD):	2.313
Pgp-substrate:	12.520451545715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.434
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.671
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	2.775
Half-life (T1/2):	0.401

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.971
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.366
Skin Sensitization:	0.097
Carcinogencity:	0.189
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC38420

Natural Product ID:	NPC38420
*Common Name:**	[(1R,4As,7E,9S,10S,11Ar)-1-Acetyloxy-4-[(1S,2R)-1,2-Diacetyloxy-4-Methylpent-3-Enyl]-10-Hydroxy-7-Methyl-11-Methylidene-4A,5,6,9,10,11A-Hexahydro-1H-Cyclonona[C]Pyran-9-Yl] Benzoate
IUPAC Name:	[(1R,4aS,7E,9S,10S,11aR)-1-acetyloxy-4-[(1S,2R)-1,2-diacetyloxy-4-methylpent-3-enyl]-10-hydroxy-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydro-1H-cyclonona[c]pyran-9-yl] benzoate
Synonyms:
Standard InCHIKey:	BQOJFPTWLOFINV-HWZARPHISA-N
Standard InCHI:	InChI=1S/C33H40O10/c1-18(2)15-28(40-21(5)34)31(41-22(6)35)26-17-39-33(42-23(7)36)29-20(4)30(37)27(16-19(3)13-14-25(26)29)43-32(38)24-11-9-8-10-12-24/h8-12,15-17,25,27-31,33,37H,4,13-14H2,1-3,5-7H3/b19-16+/t25-,27+,28-,29+,30+,31+,33-/m1/s1
SMILES:	CC(=O)O[C@H]1OC=C([C@@H]2[C@@H]1C(=C)[C@H](O)[C@H](/C=C(/CC2)C)OC(=O)c1ccccc1)[C@@H]([C@@H](C=C(C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452628
PubChem CID:	16091552
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic 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
NPO27081.1	Clavularia inflata	Under-species	n.a.	n.a.	n.a.	formosan soft coral	n.a.	PMID[17067152]

☑ 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
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.5	ug ml-1	PMID[566606]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[566606]

☑ 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 NPC38420 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	270
0.1-0.2	1010
0.2-0.3	2366
0.3-0.4	6106
0.4-0.5	10586
0.5-0.6	10100
0.6-0.7	10579
0.7-0.8	1612
0.8-0.85	62
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC136608
0.9542	High Similarity	NPC475195
0.9302	High Similarity	NPC475478
0.9084	High Similarity	NPC475569
0.8496	Intermediate Similarity	NPC148026
0.8478	Intermediate Similarity	NPC27721
0.8444	Intermediate Similarity	NPC289415
0.8444	Intermediate Similarity	NPC319995
0.8444	Intermediate Similarity	NPC17567
0.8433	Intermediate Similarity	NPC301857
0.8421	Intermediate Similarity	NPC114096
0.8406	Intermediate Similarity	NPC202729
0.8394	Intermediate Similarity	NPC28836
0.8322	Intermediate Similarity	NPC296659
0.8322	Intermediate Similarity	NPC202391
0.8321	Intermediate Similarity	NPC472248
0.8299	Intermediate Similarity	NPC289021
0.8299	Intermediate Similarity	NPC158546
0.8286	Intermediate Similarity	NPC473301
0.8273	Intermediate Similarity	NPC472374
0.8273	Intermediate Similarity	NPC472372
0.8271	Intermediate Similarity	NPC57607
0.8261	Intermediate Similarity	NPC311492
0.8261	Intermediate Similarity	NPC322503
0.8261	Intermediate Similarity	NPC470143
0.8248	Intermediate Similarity	NPC233860
0.8248	Intermediate Similarity	NPC239358
0.8248	Intermediate Similarity	NPC233692
0.8235	Intermediate Similarity	NPC27712
0.8219	Intermediate Similarity	NPC189631
0.8214	Intermediate Similarity	NPC471345
0.8201	Intermediate Similarity	NPC200154
0.8195	Intermediate Similarity	NPC138798
0.8194	Intermediate Similarity	NPC77922
0.8194	Intermediate Similarity	NPC473281
0.8151	Intermediate Similarity	NPC473149
0.8134	Intermediate Similarity	NPC246166
0.8129	Intermediate Similarity	NPC114116
0.8125	Intermediate Similarity	NPC186296
0.812	Intermediate Similarity	NPC140561
0.812	Intermediate Similarity	NPC141970
0.8112	Intermediate Similarity	NPC192658
0.8099	Intermediate Similarity	NPC87934
0.8099	Intermediate Similarity	NPC162613
0.8095	Intermediate Similarity	NPC469448
0.8092	Intermediate Similarity	NPC329997
0.8082	Intermediate Similarity	NPC473147
0.8071	Intermediate Similarity	NPC477896
0.8071	Intermediate Similarity	NPC473399
0.8071	Intermediate Similarity	NPC169398
0.8071	Intermediate Similarity	NPC473216
0.8071	Intermediate Similarity	NPC477893
0.8056	Intermediate Similarity	NPC284957
0.8054	Intermediate Similarity	NPC472658
0.8054	Intermediate Similarity	NPC474620
0.8054	Intermediate Similarity	NPC472657
0.8042	Intermediate Similarity	NPC242355
0.8041	Intermediate Similarity	NPC478236
0.8041	Intermediate Similarity	NPC478234
0.8041	Intermediate Similarity	NPC469415
0.8041	Intermediate Similarity	NPC96599
0.8028	Intermediate Similarity	NPC9905
0.8015	Intermediate Similarity	NPC290276
0.8015	Intermediate Similarity	NPC198918
0.8015	Intermediate Similarity	NPC10883
0.8015	Intermediate Similarity	NPC231888
0.8015	Intermediate Similarity	NPC10121
0.8015	Intermediate Similarity	NPC92283
0.8015	Intermediate Similarity	NPC63404
0.8015	Intermediate Similarity	NPC124878
0.8015	Intermediate Similarity	NPC204214
0.8015	Intermediate Similarity	NPC35338
0.8	Intermediate Similarity	NPC162925
0.8	Intermediate Similarity	NPC478250
0.8	Intermediate Similarity	NPC145847
0.8	Intermediate Similarity	NPC87153
0.8	Intermediate Similarity	NPC34943
0.8	Intermediate Similarity	NPC242756
0.7987	Intermediate Similarity	NPC117346
0.7987	Intermediate Similarity	NPC240592
0.7986	Intermediate Similarity	NPC159387
0.7986	Intermediate Similarity	NPC7518
0.7986	Intermediate Similarity	NPC34012
0.7986	Intermediate Similarity	NPC137501
0.7986	Intermediate Similarity	NPC154262
0.7974	Intermediate Similarity	NPC187205
0.7973	Intermediate Similarity	NPC303429
0.7973	Intermediate Similarity	NPC222102
0.7972	Intermediate Similarity	NPC472547
0.7969	Intermediate Similarity	NPC272524
0.7959	Intermediate Similarity	NPC119773
0.7959	Intermediate Similarity	NPC212808
0.7959	Intermediate Similarity	NPC208293
0.7959	Intermediate Similarity	NPC475539
0.7959	Intermediate Similarity	NPC474268
0.7959	Intermediate Similarity	NPC143246
0.7949	Intermediate Similarity	NPC109990
0.7947	Intermediate Similarity	NPC257847
0.7945	Intermediate Similarity	NPC251062
0.7945	Intermediate Similarity	NPC194938
0.7945	Intermediate Similarity	NPC471028
0.7945	Intermediate Similarity	NPC472556
0.7945	Intermediate Similarity	NPC184464
0.7941	Intermediate Similarity	NPC275576
0.7941	Intermediate Similarity	NPC28069
0.7941	Intermediate Similarity	NPC77651
0.7933	Intermediate Similarity	NPC475379
0.7931	Intermediate Similarity	NPC95449
0.7931	Intermediate Similarity	NPC91703
0.7931	Intermediate Similarity	NPC245219
0.7931	Intermediate Similarity	NPC65833
0.7931	Intermediate Similarity	NPC31081
0.7926	Intermediate Similarity	NPC471466
0.7917	Intermediate Similarity	NPC472576
0.7917	Intermediate Similarity	NPC27377
0.7917	Intermediate Similarity	NPC16912
0.7917	Intermediate Similarity	NPC77493
0.7917	Intermediate Similarity	NPC291599
0.7917	Intermediate Similarity	NPC97947
0.7917	Intermediate Similarity	NPC41481
0.7917	Intermediate Similarity	NPC87448
0.7917	Intermediate Similarity	NPC118080
0.791	Intermediate Similarity	NPC475328
0.7902	Intermediate Similarity	NPC469364
0.7902	Intermediate Similarity	NPC101686
0.7902	Intermediate Similarity	NPC65262
0.7899	Intermediate Similarity	NPC471024
0.7895	Intermediate Similarity	NPC472128
0.7895	Intermediate Similarity	NPC472127
0.7891	Intermediate Similarity	NPC240115
0.7891	Intermediate Similarity	NPC312393
0.7891	Intermediate Similarity	NPC20255
0.7891	Intermediate Similarity	NPC475528
0.7891	Intermediate Similarity	NPC158282
0.7891	Intermediate Similarity	NPC474314
0.7883	Intermediate Similarity	NPC169913
0.7881	Intermediate Similarity	NPC478235
0.7881	Intermediate Similarity	NPC34066
0.7881	Intermediate Similarity	NPC469456
0.7881	Intermediate Similarity	NPC194705
0.7881	Intermediate Similarity	NPC469398
0.7881	Intermediate Similarity	NPC469422
0.7877	Intermediate Similarity	NPC293154
0.7877	Intermediate Similarity	NPC475213
0.7877	Intermediate Similarity	NPC152796
0.7877	Intermediate Similarity	NPC38696
0.7868	Intermediate Similarity	NPC244454
0.7867	Intermediate Similarity	NPC116292
0.7867	Intermediate Similarity	NPC267469
0.7867	Intermediate Similarity	NPC179128
0.7867	Intermediate Similarity	NPC162569
0.7867	Intermediate Similarity	NPC35160
0.7867	Intermediate Similarity	NPC87630
0.7867	Intermediate Similarity	NPC35097
0.7862	Intermediate Similarity	NPC80098
0.7857	Intermediate Similarity	NPC471880
0.7857	Intermediate Similarity	NPC472394
0.7852	Intermediate Similarity	NPC120728
0.7847	Intermediate Similarity	NPC90614
0.7847	Intermediate Similarity	NPC97667
0.7847	Intermediate Similarity	NPC171207
0.7847	Intermediate Similarity	NPC324262
0.7847	Intermediate Similarity	NPC100913
0.7847	Intermediate Similarity	NPC31745
0.7847	Intermediate Similarity	NPC220936
0.7847	Intermediate Similarity	NPC275592
0.7847	Intermediate Similarity	NPC62800
0.7843	Intermediate Similarity	NPC476784
0.7842	Intermediate Similarity	NPC11025
0.7842	Intermediate Similarity	NPC475508
0.7838	Intermediate Similarity	NPC291153
0.7836	Intermediate Similarity	NPC229600
0.7832	Intermediate Similarity	NPC39549
0.7829	Intermediate Similarity	NPC229354
0.7826	Intermediate Similarity	NPC231627
0.7826	Intermediate Similarity	NPC471025
0.7823	Intermediate Similarity	NPC125882
0.7823	Intermediate Similarity	NPC96903
0.7823	Intermediate Similarity	NPC200471
0.7823	Intermediate Similarity	NPC472575
0.7823	Intermediate Similarity	NPC311825
0.7823	Intermediate Similarity	NPC177940
0.7823	Intermediate Similarity	NPC184817
0.7823	Intermediate Similarity	NPC472572
0.7823	Intermediate Similarity	NPC476973
0.7823	Intermediate Similarity	NPC174982
0.7823	Intermediate Similarity	NPC473088
0.7823	Intermediate Similarity	NPC472571
0.7823	Intermediate Similarity	NPC470157
0.7823	Intermediate Similarity	NPC25043
0.7823	Intermediate Similarity	NPC471104
0.7823	Intermediate Similarity	NPC158663
0.7823	Intermediate Similarity	NPC171525
0.7823	Intermediate Similarity	NPC29704
0.7823	Intermediate Similarity	NPC63304
0.7823	Intermediate Similarity	NPC469349
0.7823	Intermediate Similarity	NPC92867
0.7823	Intermediate Similarity	NPC472568
0.7823	Intermediate Similarity	NPC470159
0.7823	Intermediate Similarity	NPC70403

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 NPC38420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	732
0.2-0.3	1529
0.3-0.4	2725
0.4-0.5	2256
0.5-0.6	1234
0.6-0.7	412
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
0.7801	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2629	Approved
0.7444	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7685	Pre-registration
0.7385	Intermediate Similarity	NPD2182	Approved
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7325	Intermediate Similarity	NPD8455	Phase 2
0.7317	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8313	Approved
0.7305	Intermediate Similarity	NPD8312	Approved
0.7256	Intermediate Similarity	NPD7799	Discontinued
0.7226	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD969	Suspended
0.7212	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5909	Discontinued
0.7197	Intermediate Similarity	NPD2067	Discontinued
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7132	Intermediate Similarity	NPD6647	Phase 2
0.7122	Intermediate Similarity	NPD5125	Phase 3
0.7122	Intermediate Similarity	NPD5126	Approved
0.7121	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD164	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7051	Intermediate Similarity	NPD5403	Approved
0.7048	Intermediate Similarity	NPD3818	Discontinued
0.7031	Intermediate Similarity	NPD1238	Approved
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7025	Intermediate Similarity	NPD4380	Phase 2
0.7014	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7054	Approved
0.6986	Remote Similarity	NPD7008	Discontinued
0.6982	Remote Similarity	NPD8368	Discontinued
0.6982	Remote Similarity	NPD6559	Discontinued
0.6975	Remote Similarity	NPD7075	Discontinued
0.6964	Remote Similarity	NPD7472	Approved
0.6964	Remote Similarity	NPD7074	Phase 3
0.6957	Remote Similarity	NPD5402	Approved
0.6953	Remote Similarity	NPD9495	Approved
0.6947	Remote Similarity	NPD1237	Approved
0.6941	Remote Similarity	NPD7808	Phase 3
0.6937	Remote Similarity	NPD37	Approved
0.6937	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD4966	Approved
0.6914	Remote Similarity	NPD4965	Approved
0.6914	Remote Similarity	NPD4967	Phase 2
0.6913	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6908	Remote Similarity	NPD6002	Phase 3
0.6903	Remote Similarity	NPD7236	Approved
0.6901	Remote Similarity	NPD4806	Approved
0.6901	Remote Similarity	NPD4807	Approved
0.6901	Remote Similarity	NPD1091	Approved
0.6894	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4198	Discontinued
0.6882	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD5305	Approved
0.6879	Remote Similarity	NPD5306	Approved
0.687	Remote Similarity	NPD1930	Approved
0.687	Remote Similarity	NPD1929	Approved
0.687	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6653	Approved
0.686	Remote Similarity	NPD8407	Phase 2
0.6853	Remote Similarity	NPD1608	Approved
0.6845	Remote Similarity	NPD7228	Approved
0.6842	Remote Similarity	NPD6685	Approved
0.6842	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6190	Approved
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6234	Discontinued
0.6828	Remote Similarity	NPD2797	Approved
0.6824	Remote Similarity	NPD6797	Phase 2
0.6824	Remote Similarity	NPD2313	Discontinued
0.6821	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5951	Approved
0.681	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1653	Approved
0.6792	Remote Similarity	NPD7239	Suspended
0.679	Remote Similarity	NPD7819	Suspended
0.6783	Remote Similarity	NPD6287	Discontinued
0.6782	Remote Similarity	NPD8434	Phase 2
0.6781	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6085	Phase 2
0.6781	Remote Similarity	NPD5647	Approved
0.6776	Remote Similarity	NPD2799	Discontinued
0.6774	Remote Similarity	NPD3750	Approved
0.6774	Remote Similarity	NPD8166	Discontinued
0.6769	Remote Similarity	NPD2066	Phase 3
0.6767	Remote Similarity	NPD5048	Discontinued
0.6761	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6799	Approved
0.675	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8127	Discontinued
0.6738	Remote Similarity	NPD7741	Discontinued
0.6732	Remote Similarity	NPD2935	Discontinued
0.6714	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD9493	Approved
0.6713	Remote Similarity	NPD4136	Approved
0.6713	Remote Similarity	NPD4135	Approved
0.6713	Remote Similarity	NPD4106	Approved
0.6711	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7097	Phase 1
0.6711	Remote Similarity	NPD6798	Discontinued
0.6711	Remote Similarity	NPD3268	Approved
0.6708	Remote Similarity	NPD6599	Discontinued
0.6707	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD8361	Approved
0.6705	Remote Similarity	NPD8360	Approved
0.6686	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6647	Remote Similarity	NPD7199	Phase 2
0.6646	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3817	Phase 2
0.6646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3226	Approved
0.6643	Remote Similarity	NPD17	Approved
0.6641	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1551	Phase 2
0.6621	Remote Similarity	NPD6637	Approved
0.6621	Remote Similarity	NPD9717	Approved
0.6617	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5765	Approved
0.661	Remote Similarity	NPD8435	Approved
0.6608	Remote Similarity	NPD5844	Phase 1
0.6604	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8320	Phase 1
0.6595	Remote Similarity	NPD8319	Approved
0.6594	Remote Similarity	NPD6912	Phase 3
0.659	Remote Similarity	NPD7240	Approved
0.6582	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2346	Discontinued
0.6581	Remote Similarity	NPD5762	Approved
0.6581	Remote Similarity	NPD5763	Approved
0.6579	Remote Similarity	NPD1933	Approved
0.6579	Remote Similarity	NPD447	Suspended
0.6573	Remote Similarity	NPD4102	Approved
0.6573	Remote Similarity	NPD4105	Approved
0.6565	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7411	Suspended
0.6561	Remote Similarity	NPD2575	Approved
0.6561	Remote Similarity	NPD7003	Approved
0.6559	Remote Similarity	NPD7999	Approved
0.6558	Remote Similarity	NPD1510	Phase 2
0.6558	Remote Similarity	NPD3748	Approved
0.6556	Remote Similarity	NPD4062	Phase 3
0.6547	Remote Similarity	NPD7843	Approved
0.6544	Remote Similarity	NPD6686	Approved
0.6543	Remote Similarity	NPD3455	Phase 2
0.6541	Remote Similarity	NPD7435	Discontinued
0.6538	Remote Similarity	NPD7700	Phase 2
0.6538	Remote Similarity	NPD7699	Phase 2
0.6532	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7157	Approved
0.6524	Remote Similarity	NPD1934	Approved
0.6516	Remote Similarity	NPD2796	Approved
0.6516	Remote Similarity	NPD2438	Suspended
0.6515	Remote Similarity	NPD7798	Approved
0.6512	Remote Similarity	NPD1202	Approved
0.651	Remote Similarity	NPD3661	Approved
0.651	Remote Similarity	NPD3662	Phase 3
0.651	Remote Similarity	NPD3663	Approved
0.651	Remote Similarity	NPD3664	Approved
0.651	Remote Similarity	NPD5204	Approved
0.65	Remote Similarity	NPD2532	Approved
0.65	Remote Similarity	NPD2533	Approved
0.65	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2534	Approved
0.6491	Remote Similarity	NPD7473	Discontinued
0.6486	Remote Similarity	NPD2159	Approved
0.6486	Remote Similarity	NPD2628	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