NPASS Compound

Structure

CID318363 OpenBabel06191716142D 41 42 0 0 1 0 0 0 0 0999 V2000 5.0817 -2.8179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0162 -3.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2052 -9.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0951 -0.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8872 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6071 -7.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0138 -4.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2052 -6.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.7294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6998 -4.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7216 -4.5121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3689 -3.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4344 -3.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1254 -2.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -5.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -8.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -4.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -7.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6561 -6.7539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4126 -3.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3470 -4.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0712 -9.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0683 -5.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 -6.4449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6071 -6.4449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1473 -2.1942 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.2052 -7.9449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6561 -5.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7052 -6.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8383 -1.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4731 -6.9449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6071 -5.4449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2052 -6.9449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9372 -9.9449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0683 -5.9449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7052 -6.0789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2052 -5.2128 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.5074 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -2.9373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0712 -8.4449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 0.0424 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 9 39 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 32 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 21 28 2 0 0 0 0 22 34 2 0 0 0 0 22 40 1 0 0 0 0 23 28 1 0 0 0 0 23 35 2 0 0 0 0 24 31 1 1 0 0 0 24 33 1 0 0 0 0 25 31 1 6 0 0 0 25 32 1 0 0 0 0 26 30 1 0 0 0 0 26 39 1 0 0 0 0 27 33 1 6 0 0 0 27 40 1 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 29 36 2 0 0 0 0 29 37 1 0 0 0 0 30 38 1 0 0 0 0 31 6 1 1 0 0 0 32 7 1 6 0 0 0 33 8 1 6 0 0 0 M CHG 2 37 -1 41 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	555.33
Volume:	595.413
LogP:	2.406
LogD:	0.813
LogS:	-4.262
# Rotatable Bonds:	9
TPSA:	112.96
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	5.34
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975
MDCK Permeability:	2.522220165701583e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	91.1330337524414%
Volume Distribution (VD):	0.429
Pgp-substrate:	9.074601173400879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.421
CYP3A4-substrate:	0.592

ADMET: Excretion

Clearance (CL):	1.57
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.303
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.481
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.915
Carcinogencity:	0.092
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC318363

Natural Product ID:	NPC318363
*Common Name:**	Globostellatic Acid C
IUPAC Name:	sodium;(3Z,3aS,5aR,6R,7R,9aR,9bS)-7-acetyloxy-3-[(3E,5E,7E)-10-hydroxy-9-methoxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms:	Globostellatic Acid C
Standard InCHIKey:	GMHCRJAKMQQTJB-RLOWDUIGSA-M
Standard InCHI:	InChI=1S/C33H48O7.Na/c1-20(13-14-26(39-9)30(4,5)38)11-10-12-21(2)28-23(35)19-25-31(6)18-16-27(40-22(3)34)33(8,29(36)37)24(31)15-17-32(25,28)7;/h10-14,24-27,38H,15-19H2,1-9H3,(H,36,37);/q;+1/p-1/b12-10+,14-13+,20-11+,28-21+;/t24-,25+,26?,27-,31+,32+,33-;/m1./s1
SMILES:	CC(=CC=CC(=C1C(=O)CC2C1(CCC3C2(CCC(C3(C)C(=O)[O-])OC(=O)C)C)C)C)C=CC(C(C)(C)O)OC.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455797
PubChem CID:	23682809
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO10924	Stelletta globostellata	Species	Ancorinidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.46	ug.mL-1	PMID[522926]

☑ 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 NPC318363 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	200
0.1-0.2	978
0.2-0.3	3378
0.3-0.4	6518
0.4-0.5	13743
0.5-0.6	7615
0.6-0.7	7240
0.7-0.8	2830
0.8-0.85	150
0.85-0.9	28
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475418
1.0	High Similarity	NPC473482
0.99	High Similarity	NPC475065
0.97	High Similarity	NPC329048
0.97	High Similarity	NPC330011
0.9505	High Similarity	NPC473284
0.94	High Similarity	NPC473283
0.94	High Similarity	NPC329345
0.94	High Similarity	NPC475526
0.93	High Similarity	NPC114540
0.93	High Similarity	NPC155332
0.93	High Similarity	NPC32577
0.9208	High Similarity	NPC475050
0.9208	High Similarity	NPC72151
0.9109	High Similarity	NPC320447
0.9091	High Similarity	NPC110937
0.901	High Similarity	NPC115899
0.8911	High Similarity	NPC266955
0.89	High Similarity	NPC2049
0.8824	High Similarity	NPC282524
0.8812	High Similarity	NPC57079
0.8812	High Similarity	NPC108368
0.88	High Similarity	NPC471153
0.8788	High Similarity	NPC473431
0.8788	High Similarity	NPC471078
0.8788	High Similarity	NPC473435
0.8788	High Similarity	NPC473280
0.8727	High Similarity	NPC470492
0.8727	High Similarity	NPC286528
0.8727	High Similarity	NPC20302
0.8727	High Similarity	NPC140055
0.8727	High Similarity	NPC167606
0.8725	High Similarity	NPC35751
0.8716	High Similarity	NPC147912
0.8716	High Similarity	NPC67259
0.8713	High Similarity	NPC474938
0.8713	High Similarity	NPC474785
0.87	High Similarity	NPC88310
0.8667	High Similarity	NPC266570
0.8649	High Similarity	NPC473617
0.8649	High Similarity	NPC50774
0.8649	High Similarity	NPC473828
0.8649	High Similarity	NPC709
0.8611	High Similarity	NPC474315
0.8598	High Similarity	NPC173905
0.8598	High Similarity	NPC5475
0.8598	High Similarity	NPC472216
0.8598	High Similarity	NPC284828
0.8571	High Similarity	NPC473175
0.8571	High Similarity	NPC264954
0.8559	High Similarity	NPC183580
0.8559	High Similarity	NPC470493
0.8559	High Similarity	NPC312824
0.8545	High Similarity	NPC475163
0.8496	Intermediate Similarity	NPC474370
0.8491	Intermediate Similarity	NPC477125
0.8485	Intermediate Similarity	NPC161638
0.8476	Intermediate Similarity	NPC180204
0.8462	Intermediate Similarity	NPC194028
0.8462	Intermediate Similarity	NPC168319
0.8455	Intermediate Similarity	NPC122056
0.8447	Intermediate Similarity	NPC316598
0.8431	Intermediate Similarity	NPC122324
0.8431	Intermediate Similarity	NPC106425
0.8431	Intermediate Similarity	NPC301534
0.8431	Intermediate Similarity	NPC250757
0.8431	Intermediate Similarity	NPC151725
0.8426	Intermediate Similarity	NPC10064
0.8426	Intermediate Similarity	NPC170221
0.8421	Intermediate Similarity	NPC67569
0.8416	Intermediate Similarity	NPC474690
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.8393	Intermediate Similarity	NPC476965
0.8393	Intermediate Similarity	NPC470959
0.8381	Intermediate Similarity	NPC473163
0.8364	Intermediate Similarity	NPC470063
0.8364	Intermediate Similarity	NPC191620
0.8362	Intermediate Similarity	NPC470494
0.8362	Intermediate Similarity	NPC3381
0.835	Intermediate Similarity	NPC73911
0.8349	Intermediate Similarity	NPC6206
0.8349	Intermediate Similarity	NPC16270
0.8349	Intermediate Similarity	NPC29133
0.8348	Intermediate Similarity	NPC170538
0.8348	Intermediate Similarity	NPC23786
0.8348	Intermediate Similarity	NPC88326
0.8348	Intermediate Similarity	NPC153700
0.8348	Intermediate Similarity	NPC470265
0.8333	Intermediate Similarity	NPC209355
0.8333	Intermediate Similarity	NPC306265
0.8333	Intermediate Similarity	NPC220155
0.8333	Intermediate Similarity	NPC180950
0.8319	Intermediate Similarity	NPC257457
0.8319	Intermediate Similarity	NPC311554
0.8319	Intermediate Similarity	NPC186525
0.8318	Intermediate Similarity	NPC475414
0.8318	Intermediate Similarity	NPC173172
0.8304	Intermediate Similarity	NPC270929
0.8304	Intermediate Similarity	NPC64318
0.8302	Intermediate Similarity	NPC324001
0.8302	Intermediate Similarity	NPC23584
0.8302	Intermediate Similarity	NPC112009
0.83	Intermediate Similarity	NPC475965
0.83	Intermediate Similarity	NPC474842
0.8291	Intermediate Similarity	NPC473635
0.8286	Intermediate Similarity	NPC303559
0.8286	Intermediate Similarity	NPC93744
0.8286	Intermediate Similarity	NPC476888
0.8276	Intermediate Similarity	NPC469789
0.8276	Intermediate Similarity	NPC11895
0.8273	Intermediate Similarity	NPC324683
0.8273	Intermediate Similarity	NPC470961
0.8269	Intermediate Similarity	NPC278386
0.8269	Intermediate Similarity	NPC124512
0.8269	Intermediate Similarity	NPC159763
0.8252	Intermediate Similarity	NPC242848
0.8246	Intermediate Similarity	NPC473274
0.8246	Intermediate Similarity	NPC305260
0.8246	Intermediate Similarity	NPC270850
0.8241	Intermediate Similarity	NPC255387
0.8241	Intermediate Similarity	NPC475294
0.8241	Intermediate Similarity	NPC131665
0.8241	Intermediate Similarity	NPC475176
0.8235	Intermediate Similarity	NPC299100
0.8235	Intermediate Similarity	NPC38830
0.8218	Intermediate Similarity	NPC473986
0.8218	Intermediate Similarity	NPC474018
0.8218	Intermediate Similarity	NPC303697
0.8214	Intermediate Similarity	NPC284915
0.8208	Intermediate Similarity	NPC40918
0.8208	Intermediate Similarity	NPC11956
0.8208	Intermediate Similarity	NPC476081
0.8208	Intermediate Similarity	NPC476890
0.8205	Intermediate Similarity	NPC8369
0.8205	Intermediate Similarity	NPC8374
0.8205	Intermediate Similarity	NPC81736
0.8205	Intermediate Similarity	NPC172154
0.8198	Intermediate Similarity	NPC269530
0.8198	Intermediate Similarity	NPC69291
0.819	Intermediate Similarity	NPC117685
0.819	Intermediate Similarity	NPC473510
0.819	Intermediate Similarity	NPC474012
0.819	Intermediate Similarity	NPC476299
0.8182	Intermediate Similarity	NPC473627
0.8182	Intermediate Similarity	NPC472215
0.8182	Intermediate Similarity	NPC472214
0.8174	Intermediate Similarity	NPC476962
0.8174	Intermediate Similarity	NPC476961
0.8173	Intermediate Similarity	NPC253826
0.8165	Intermediate Similarity	NPC472218
0.8165	Intermediate Similarity	NPC472825
0.8165	Intermediate Similarity	NPC472217
0.8165	Intermediate Similarity	NPC472219
0.8158	Intermediate Similarity	NPC329736
0.8155	Intermediate Similarity	NPC180557
0.8155	Intermediate Similarity	NPC37787
0.8155	Intermediate Similarity	NPC473415
0.8155	Intermediate Similarity	NPC469329
0.8155	Intermediate Similarity	NPC30677
0.8148	Intermediate Similarity	NPC469874
0.8148	Intermediate Similarity	NPC189863
0.8148	Intermediate Similarity	NPC34768
0.8137	Intermediate Similarity	NPC205034
0.8137	Intermediate Similarity	NPC152778
0.8137	Intermediate Similarity	NPC139692
0.8137	Intermediate Similarity	NPC162615
0.8136	Intermediate Similarity	NPC293112
0.8131	Intermediate Similarity	NPC120321
0.8131	Intermediate Similarity	NPC476889
0.8125	Intermediate Similarity	NPC471204
0.812	Intermediate Similarity	NPC120724
0.812	Intermediate Similarity	NPC6193
0.8113	Intermediate Similarity	NPC473174
0.8113	Intermediate Similarity	NPC476897
0.8103	Intermediate Similarity	NPC46570
0.8103	Intermediate Similarity	NPC470878
0.8103	Intermediate Similarity	NPC473256
0.81	Intermediate Similarity	NPC310752
0.81	Intermediate Similarity	NPC292491
0.81	Intermediate Similarity	NPC473879
0.8095	Intermediate Similarity	NPC98868
0.8095	Intermediate Similarity	NPC278008
0.8091	Intermediate Similarity	NPC41405
0.8087	Intermediate Similarity	NPC61520
0.8087	Intermediate Similarity	NPC473839
0.8087	Intermediate Similarity	NPC77689
0.8087	Intermediate Similarity	NPC211093
0.8087	Intermediate Similarity	NPC473270
0.8087	Intermediate Similarity	NPC473636
0.8087	Intermediate Similarity	NPC470186
0.8083	Intermediate Similarity	NPC476966
0.8077	Intermediate Similarity	NPC327788
0.8077	Intermediate Similarity	NPC473153
0.8077	Intermediate Similarity	NPC16967
0.8073	Intermediate Similarity	NPC471783
0.8073	Intermediate Similarity	NPC302788
0.8073	Intermediate Similarity	NPC9457
0.8073	Intermediate Similarity	NPC473173
0.8073	Intermediate Similarity	NPC179380

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 NPC318363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1128
0.2-0.3	3255
0.3-0.4	2827
0.4-0.5	1122
0.5-0.6	319
0.6-0.7	217
0.7-0.8	111
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD7115	Discovery
0.8269	Intermediate Similarity	NPD4225	Approved
0.7925	Intermediate Similarity	NPD7638	Approved
0.7876	Intermediate Similarity	NPD8297	Approved
0.785	Intermediate Similarity	NPD7639	Approved
0.785	Intermediate Similarity	NPD7640	Approved
0.7714	Intermediate Similarity	NPD7748	Approved
0.7679	Intermediate Similarity	NPD6881	Approved
0.7679	Intermediate Similarity	NPD6899	Approved
0.7658	Intermediate Similarity	NPD7128	Approved
0.7658	Intermediate Similarity	NPD6675	Approved
0.7658	Intermediate Similarity	NPD5739	Approved
0.7658	Intermediate Similarity	NPD6402	Approved
0.7632	Intermediate Similarity	NPD8130	Phase 1
0.7619	Intermediate Similarity	NPD6399	Phase 3
0.7589	Intermediate Similarity	NPD5697	Approved
0.7563	Intermediate Similarity	NPD6319	Approved
0.7544	Intermediate Similarity	NPD7290	Approved
0.7544	Intermediate Similarity	NPD6883	Approved
0.7544	Intermediate Similarity	NPD7102	Approved
0.7524	Intermediate Similarity	NPD7637	Suspended
0.7522	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7478	Intermediate Similarity	NPD6650	Approved
0.7478	Intermediate Similarity	NPD6617	Approved
0.7478	Intermediate Similarity	NPD6869	Approved
0.7478	Intermediate Similarity	NPD6649	Approved
0.7478	Intermediate Similarity	NPD6847	Approved
0.7456	Intermediate Similarity	NPD6373	Approved
0.7456	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6372	Approved
0.7456	Intermediate Similarity	NPD6014	Approved
0.7456	Intermediate Similarity	NPD6012	Approved
0.7456	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD5701	Approved
0.7429	Intermediate Similarity	NPD5785	Approved
0.7414	Intermediate Similarity	NPD6882	Approved
0.7398	Intermediate Similarity	NPD7507	Approved
0.7379	Intermediate Similarity	NPD7146	Approved
0.7379	Intermediate Similarity	NPD6409	Approved
0.7379	Intermediate Similarity	NPD3618	Phase 1
0.7379	Intermediate Similarity	NPD6684	Approved
0.7379	Intermediate Similarity	NPD7521	Approved
0.7379	Intermediate Similarity	NPD7334	Approved
0.7379	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6011	Approved
0.7368	Intermediate Similarity	NPD6686	Approved
0.7358	Intermediate Similarity	NPD6411	Approved
0.7358	Intermediate Similarity	NPD6079	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.735	Intermediate Similarity	NPD4632	Approved
0.7333	Intermediate Similarity	NPD5328	Approved
0.7327	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7492	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.729	Intermediate Similarity	NPD5778	Approved
0.729	Intermediate Similarity	NPD5779	Approved
0.7282	Intermediate Similarity	NPD1694	Approved
0.728	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD5696	Approved
0.7258	Intermediate Similarity	NPD6616	Approved
0.7241	Intermediate Similarity	NPD4634	Approved
0.7241	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5737	Approved
0.7238	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6903	Approved
0.7238	Intermediate Similarity	NPD6672	Approved
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7232	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8033	Approved
0.7213	Intermediate Similarity	NPD7503	Approved
0.7212	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5285	Approved
0.7207	Intermediate Similarity	NPD4696	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.72	Intermediate Similarity	NPD7078	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7196	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD5281	Approved
0.7196	Intermediate Similarity	NPD5693	Phase 1
0.7196	Intermediate Similarity	NPD8035	Phase 2
0.7196	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD4786	Approved
0.7182	Intermediate Similarity	NPD4755	Approved
0.7179	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6101	Approved
0.717	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3667	Approved
0.7156	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6370	Approved
0.7131	Intermediate Similarity	NPD8377	Approved
0.7131	Intermediate Similarity	NPD8294	Approved
0.7131	Intermediate Similarity	NPD6059	Approved
0.713	Intermediate Similarity	NPD4202	Approved
0.713	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7107	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD5141	Approved
0.7094	Intermediate Similarity	NPD6371	Approved
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5224	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD4633	Approved
0.708	Intermediate Similarity	NPD5225	Approved
0.7073	Intermediate Similarity	NPD6016	Approved
0.7073	Intermediate Similarity	NPD8296	Approved
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD8378	Approved
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD6015	Approved
0.7073	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8380	Approved
0.7073	Intermediate Similarity	NPD8335	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD6648	Approved
0.7054	Intermediate Similarity	NPD4700	Approved
0.7049	Intermediate Similarity	NPD7101	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7049	Intermediate Similarity	NPD7100	Approved
0.7043	Intermediate Similarity	NPD6008	Approved
0.7037	Intermediate Similarity	NPD6050	Approved
0.7037	Intermediate Similarity	NPD7983	Approved
0.7037	Intermediate Similarity	NPD5694	Approved
0.7027	Intermediate Similarity	NPD5173	Approved
0.7025	Intermediate Similarity	NPD6009	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7019	Intermediate Similarity	NPD3133	Approved
0.7018	Intermediate Similarity	NPD5175	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7016	Intermediate Similarity	NPD5988	Approved
0.7009	Intermediate Similarity	NPD4753	Phase 2
0.7009	Intermediate Similarity	NPD6080	Approved
0.7009	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5223	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.6983	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3573	Approved
0.6981	Remote Similarity	NPD7524	Approved
0.6967	Remote Similarity	NPD6335	Approved
0.696	Remote Similarity	NPD8328	Phase 3
0.696	Remote Similarity	NPD7604	Phase 2
0.6952	Remote Similarity	NPD5363	Approved
0.6952	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6698	Approved
0.6944	Remote Similarity	NPD46	Approved
0.6944	Remote Similarity	NPD5692	Phase 3
0.6944	Remote Similarity	NPD5207	Approved
0.6944	Remote Similarity	NPD7838	Discovery
0.6942	Remote Similarity	NPD6274	Approved
0.6942	Remote Similarity	NPD6868	Approved
0.6937	Remote Similarity	NPD4697	Phase 3
0.6935	Remote Similarity	NPD5983	Phase 2
0.6917	Remote Similarity	NPD8133	Approved
0.6893	Remote Similarity	NPD5369	Approved
0.6887	Remote Similarity	NPD5279	Phase 3
0.6885	Remote Similarity	NPD6317	Approved
0.6857	Remote Similarity	NPD3668	Phase 3
0.6852	Remote Similarity	NPD6051	Approved
0.6852	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6336	Discontinued
0.6847	Remote Similarity	NPD4629	Approved
0.6847	Remote Similarity	NPD5210	Approved
0.6846	Remote Similarity	NPD7260	Phase 2
0.6833	Remote Similarity	NPD6053	Discontinued
0.6829	Remote Similarity	NPD6313	Approved
0.6829	Remote Similarity	NPD6314	Approved
0.6827	Remote Similarity	NPD5209	Approved
0.6827	Remote Similarity	NPD4269	Approved
0.6827	Remote Similarity	NPD4270	Approved
0.6827	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD4221	Approved
0.68	Remote Similarity	NPD8039	Approved
0.68	Remote Similarity	NPD6909	Approved
0.68	Remote Similarity	NPD6908	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD5329	Approved
0.678	Remote Similarity	NPD4730	Approved
0.678	Remote Similarity	NPD4729	Approved
0.6765	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6695	Phase 3
0.6759	Remote Similarity	NPD5208	Approved
0.6757	Remote Similarity	NPD6001	Approved
0.6752	Remote Similarity	NPD4768	Approved
0.6752	Remote Similarity	NPD4767	Approved
0.6733	Remote Similarity	NPD6933	Approved
0.6729	Remote Similarity	NPD4519	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data