NPASS Compound

Structure

NPC473503 OpenBabel07101718332D 46 50 0 0 1 0 0 0 0 0999 V2000 5.5000 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3662 -7.0895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3446 -5.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8525 -8.4278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6230 -6.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1093 -7.7587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8799 -5.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0114 -7.1406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0878 -3.1551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7330 -4.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -3.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.8035 -8.1188 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.5000 -3.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.2683 -6.4715 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0388 -3.4641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.4762 -5.4933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -2.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -4.8301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.5741 -6.1114 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -3.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -4.8301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0388 -4.4641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -3.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.3172 -6.7805 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0878 -4.7731 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.7820 -5.1332 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.5467 -8.7879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8479 -2.8763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4272 -5.1843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9899 -4.1551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -6.6962 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -5.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -5.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.6962 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 42 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 24 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 31 1 0 0 0 0 12 32 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 33 1 0 0 0 0 16 25 1 0 0 0 0 16 43 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 19 34 1 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 29 1 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 44 1 0 0 0 0 25 28 1 0 0 0 0 25 45 1 0 0 0 0 26 31 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 37 1 0 0 0 0 28 42 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 30 43 1 0 0 0 0 30 44 1 0 0 0 0 33 38 1 0 0 0 0 39 46 1 0 0 0 0 40 46 2 0 0 0 0 41 46 2 0 0 0 0 45 46 1 0 0 0 0 M CHG 1 39 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	677.36
Volume:	659.215
LogP:	2.687
LogD:	2.711
LogS:	-3.303
# Rotatable Bonds:	10
TPSA:	195.27
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	5.899
Fsp3:	1.0
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:	-5.108
MDCK Permeability:	1.7577956896275282e-05
Pgp-inhibitor:	0.815
Pgp-substrate:	0.538
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.448

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	91.66242218017578%
Volume Distribution (VD):	0.7
Pgp-substrate:	6.984557151794434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	1.941
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.509
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.748
Skin Sensitization:	0.934
Carcinogencity:	0.445
Eye Corrosion:	0.08
Eye Irritation:	0.023
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC473503

Natural Product ID:	NPC473503
*Common Name:**	Phrygioside B
IUPAC Name:	sodium;[(3R,4R,5R,6S)-5-hydroxy-4-methoxy-6-[(3S,6R)-2-methyl-6-[(3S,5S,6S,8S,9R,10S,13R,14S,15S,17R)-3,6,8,15-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]heptan-3-yl]oxyoxan-3-yl] sulfate
Synonyms:	phrygioside B
Standard InCHIKey:	YQYQOMMAYSIATB-QTNWXOGTSA-M
Standard InCHI:	InChI=1S/C33H58O12S.Na/c1-17(2)24(44-30-27(37)28(42-6)25(16-43-30)45-46(39,40)41)8-7-18(3)20-14-22(35)29-32(20,5)12-10-26-31(4)11-9-19(34)13-21(31)23(36)15-33(26,29)38;/h17-30,34-38H,7-16H2,1-6H3,(H,39,40,41);/q;+1/p-1/t18-,19+,20-,21-,22+,23+,24+,25-,26-,27-,28+,29-,30+,31+,32-,33+;/m1./s1
SMILES:	CC(C)C(CCC(C)C1CC(C2C1(CCC3C2(CC(C4C3(CCC(C4)O)C)O)O)C)O)OC5C(C(C(CO5)OS(=O)(=O)[O-])OC)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443944
PubChem CID:	23676867
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO27636	Hippasteria phrygiana	Species	Goniasteridae	Eukaryota	n.a.	pacific	n.a.	PMID[16252922]
NPO27636	Hippasteria phrygiana	Species	Goniasteridae	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
EC50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1490	Cell Line	Ehrlich	Mus musculus	EC50	=	70.0	ug.mL-1	PMID[503786]
NPT2	Others	Unspecified		EC50	=	20.0	ug.mL-1	PMID[503786]

☑ 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 NPC473503 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	562
0.1-0.2	5060
0.2-0.3	13263
0.3-0.4	10981
0.4-0.5	5539
0.5-0.6	3721
0.6-0.7	2336
0.7-0.8	942
0.8-0.85	158
0.85-0.9	100
0.9-0.95	27
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC469710
0.9775	High Similarity	NPC473287
0.977	High Similarity	NPC476668
0.977	High Similarity	NPC473637
0.9659	High Similarity	NPC476669
0.9655	High Similarity	NPC279329
0.956	High Similarity	NPC473638
0.9551	High Similarity	NPC475325
0.9545	High Similarity	NPC293609
0.9545	High Similarity	NPC36372
0.9438	High Similarity	NPC311246
0.9438	High Similarity	NPC277774
0.9438	High Similarity	NPC167644
0.9425	High Similarity	NPC281004
0.9355	High Similarity	NPC477225
0.9348	High Similarity	NPC473616
0.9333	High Similarity	NPC3538
0.9333	High Similarity	NPC309866
0.9333	High Similarity	NPC477224
0.9333	High Similarity	NPC113500
0.9326	High Similarity	NPC204881
0.9326	High Similarity	NPC473830
0.9318	High Similarity	NPC102725
0.9318	High Similarity	NPC473472
0.931	High Similarity	NPC43912
0.931	High Similarity	NPC140446
0.9231	High Similarity	NPC92196
0.9213	High Similarity	NPC473542
0.9213	High Similarity	NPC223143
0.9213	High Similarity	NPC65550
0.9121	High Similarity	NPC24960
0.9121	High Similarity	NPC473774
0.9121	High Similarity	NPC252253
0.9121	High Similarity	NPC45959
0.9121	High Similarity	NPC175
0.9111	High Similarity	NPC149966
0.9111	High Similarity	NPC5632
0.9101	High Similarity	NPC82955
0.9101	High Similarity	NPC131466
0.908	High Similarity	NPC290612
0.9032	High Similarity	NPC477222
0.9032	High Similarity	NPC477223
0.9022	High Similarity	NPC473065
0.9022	High Similarity	NPC473067
0.9022	High Similarity	NPC473064
0.9011	High Similarity	NPC137004
0.9011	High Similarity	NPC149400
0.9011	High Similarity	NPC88962
0.9011	High Similarity	NPC473726
0.9011	High Similarity	NPC172838
0.9011	High Similarity	NPC144790
0.8925	High Similarity	NPC142264
0.8925	High Similarity	NPC304011
0.8925	High Similarity	NPC139271
0.8925	High Similarity	NPC476510
0.8925	High Similarity	NPC296936
0.8913	High Similarity	NPC131693
0.8913	High Similarity	NPC174024
0.8913	High Similarity	NPC253268
0.8913	High Similarity	NPC291547
0.8913	High Similarity	NPC473851
0.8913	High Similarity	NPC179859
0.8913	High Similarity	NPC475436
0.8913	High Similarity	NPC312678
0.8901	High Similarity	NPC210759
0.8901	High Similarity	NPC307167
0.8901	High Similarity	NPC229801
0.8889	High Similarity	NPC20822
0.8876	High Similarity	NPC472396
0.883	High Similarity	NPC470028
0.883	High Similarity	NPC233649
0.8817	High Similarity	NPC474399
0.8817	High Similarity	NPC477494
0.8804	High Similarity	NPC325828
0.8804	High Similarity	NPC250393
0.8804	High Similarity	NPC477547
0.8804	High Similarity	NPC48339
0.8804	High Similarity	NPC297348
0.8804	High Similarity	NPC141769
0.8804	High Similarity	NPC477451
0.8804	High Similarity	NPC177834
0.8804	High Similarity	NPC249204
0.8804	High Similarity	NPC234352
0.8788	High Similarity	NPC475634
0.875	High Similarity	NPC475574
0.8723	High Similarity	NPC121453
0.871	High Similarity	NPC305418
0.871	High Similarity	NPC191915
0.871	High Similarity	NPC264101
0.871	High Similarity	NPC291203
0.871	High Similarity	NPC222731
0.871	High Similarity	NPC30687
0.871	High Similarity	NPC294686
0.871	High Similarity	NPC217205
0.871	High Similarity	NPC471464
0.871	High Similarity	NPC151214
0.87	High Similarity	NPC474573
0.8696	High Similarity	NPC59006
0.8632	High Similarity	NPC470591
0.8632	High Similarity	NPC475207
0.8632	High Similarity	NPC307534
0.8632	High Similarity	NPC476112
0.8632	High Similarity	NPC274200
0.8617	High Similarity	NPC94582
0.8617	High Similarity	NPC19400
0.8617	High Similarity	NPC473727
0.8617	High Similarity	NPC6295
0.8617	High Similarity	NPC107962
0.8617	High Similarity	NPC475351
0.8617	High Similarity	NPC57964
0.8617	High Similarity	NPC206003
0.8617	High Similarity	NPC107188
0.8617	High Similarity	NPC211354
0.8617	High Similarity	NPC473610
0.8557	High Similarity	NPC476512
0.8557	High Similarity	NPC472081
0.8557	High Similarity	NPC108227
0.8557	High Similarity	NPC477172
0.8557	High Similarity	NPC476839
0.8557	High Similarity	NPC476838
0.8557	High Similarity	NPC478106
0.8556	High Similarity	NPC471240
0.8542	High Similarity	NPC473518
0.8539	High Similarity	NPC474156
0.8526	High Similarity	NPC84111
0.8526	High Similarity	NPC470866
0.8526	High Similarity	NPC475625
0.8526	High Similarity	NPC473601
0.8526	High Similarity	NPC98018
0.8526	High Similarity	NPC132080
0.8526	High Similarity	NPC470863
0.8526	High Similarity	NPC160426
0.8526	High Similarity	NPC237071
0.8526	High Similarity	NPC470865
0.8526	High Similarity	NPC232037
0.8526	High Similarity	NPC184617
0.8526	High Similarity	NPC470864
0.8526	High Similarity	NPC238796
0.8526	High Similarity	NPC472989
0.8526	High Similarity	NPC103616
0.8526	High Similarity	NPC97700
0.8526	High Similarity	NPC128572
0.8526	High Similarity	NPC30856
0.8526	High Similarity	NPC195297
0.8526	High Similarity	NPC252056
0.8526	High Similarity	NPC475643
0.8526	High Similarity	NPC116756
0.8526	High Similarity	NPC287483
0.8526	High Similarity	NPC284104
0.8526	High Similarity	NPC203434
0.8485	Intermediate Similarity	NPC475521
0.8478	Intermediate Similarity	NPC228059
0.8469	Intermediate Similarity	NPC134967
0.8469	Intermediate Similarity	NPC114700
0.8469	Intermediate Similarity	NPC310138
0.8469	Intermediate Similarity	NPC470029
0.8462	Intermediate Similarity	NPC161928
0.8462	Intermediate Similarity	NPC210658
0.8454	Intermediate Similarity	NPC470030
0.8454	Intermediate Similarity	NPC41843
0.8447	Intermediate Similarity	NPC475354
0.8447	Intermediate Similarity	NPC475312
0.8444	Intermediate Similarity	NPC232044
0.8444	Intermediate Similarity	NPC273290
0.8438	Intermediate Similarity	NPC210157
0.8438	Intermediate Similarity	NPC232611
0.8438	Intermediate Similarity	NPC470861
0.8438	Intermediate Similarity	NPC115165
0.8438	Intermediate Similarity	NPC470862
0.8438	Intermediate Similarity	NPC83137
0.8438	Intermediate Similarity	NPC51520
0.8438	Intermediate Similarity	NPC303069
0.8427	Intermediate Similarity	NPC241959
0.8384	Intermediate Similarity	NPC97260
0.8384	Intermediate Similarity	NPC476837
0.8384	Intermediate Similarity	NPC139181
0.837	Intermediate Similarity	NPC128475
0.8367	Intermediate Similarity	NPC31346
0.8351	Intermediate Similarity	NPC291548
0.8333	Intermediate Similarity	NPC156377
0.8333	Intermediate Similarity	NPC227260
0.8315	Intermediate Similarity	NPC296734
0.8315	Intermediate Similarity	NPC470611
0.8276	Intermediate Similarity	NPC177343
0.8265	Intermediate Similarity	NPC20028
0.8247	Intermediate Similarity	NPC76486
0.8229	Intermediate Similarity	NPC215570
0.8222	Intermediate Similarity	NPC478054
0.8211	Intermediate Similarity	NPC323231
0.8211	Intermediate Similarity	NPC470623
0.8211	Intermediate Similarity	NPC224003
0.8211	Intermediate Similarity	NPC171741
0.8211	Intermediate Similarity	NPC18724
0.82	Intermediate Similarity	NPC34562
0.8182	Intermediate Similarity	NPC472023
0.8182	Intermediate Similarity	NPC47566
0.8182	Intermediate Similarity	NPC88000
0.8182	Intermediate Similarity	NPC4831
0.8182	Intermediate Similarity	NPC309425
0.8182	Intermediate Similarity	NPC129372

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 NPC473503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	506
0.1-0.2	4611
0.2-0.3	2828
0.3-0.4	631
0.4-0.5	297
0.5-0.6	219
0.6-0.7	41
0.7-0.8	16
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8804	High Similarity	NPD8171	Discontinued
0.809	Intermediate Similarity	NPD6928	Phase 2
0.7941	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7327	Approved
0.7411	Intermediate Similarity	NPD7328	Approved
0.7368	Intermediate Similarity	NPD8380	Approved
0.7368	Intermediate Similarity	NPD8379	Approved
0.7368	Intermediate Similarity	NPD8296	Approved
0.7368	Intermediate Similarity	NPD8335	Approved
0.7368	Intermediate Similarity	NPD8378	Approved
0.7356	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7516	Approved
0.7281	Intermediate Similarity	NPD8294	Approved
0.7281	Intermediate Similarity	NPD8377	Approved
0.7217	Intermediate Similarity	NPD8033	Approved
0.7207	Intermediate Similarity	NPD8133	Approved
0.7157	Intermediate Similarity	NPD7991	Discontinued
0.7033	Intermediate Similarity	NPD1811	Approved
0.7033	Intermediate Similarity	NPD1810	Approved
0.6833	Remote Similarity	NPD7507	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD7319	Approved
0.678	Remote Similarity	NPD7503	Approved
0.6703	Remote Similarity	NPD4787	Phase 1
0.6703	Remote Similarity	NPD2686	Approved
0.6703	Remote Similarity	NPD2687	Approved
0.6703	Remote Similarity	NPD2254	Approved
0.6703	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6940	Discontinued
0.6607	Remote Similarity	NPD8174	Phase 2
0.6591	Remote Similarity	NPD371	Approved
0.6566	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3669	Approved
0.6562	Remote Similarity	NPD6118	Approved
0.6562	Remote Similarity	NPD6115	Approved
0.6562	Remote Similarity	NPD6697	Approved
0.6562	Remote Similarity	NPD6114	Approved
0.6458	Remote Similarity	NPD6116	Phase 1
0.6452	Remote Similarity	NPD7736	Approved
0.6441	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6117	Approved
0.6311	Remote Similarity	NPD6370	Approved
0.6263	Remote Similarity	NPD7525	Registered
0.624	Remote Similarity	NPD8293	Discontinued
0.6148	Remote Similarity	NPD6054	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6146	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6700	Approved
0.6129	Remote Similarity	NPD8328	Phase 3
0.6124	Remote Similarity	NPD8449	Approved
0.6105	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3702	Approved
0.6082	Remote Similarity	NPD3703	Phase 2
0.6077	Remote Similarity	NPD8450	Suspended
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD6702	Approved
0.6075	Remote Similarity	NPD8035	Phase 2
0.6075	Remote Similarity	NPD6703	Approved
0.6034	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD4245	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5966	Remote Similarity	NPD6882	Approved
0.5966	Remote Similarity	NPD8297	Approved
0.5952	Remote Similarity	NPD7492	Approved
0.5929	Remote Similarity	NPD1700	Approved
0.592	Remote Similarity	NPD5988	Approved
0.5906	Remote Similarity	NPD6616	Approved
0.5902	Remote Similarity	NPD6009	Approved
0.59	Remote Similarity	NPD5364	Discontinued
0.5899	Remote Similarity	NPD7625	Phase 1
0.5897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3698	Phase 2
0.5893	Remote Similarity	NPD7638	Approved
0.5887	Remote Similarity	NPD6319	Approved
0.5882	Remote Similarity	NPD1780	Approved
0.5882	Remote Similarity	NPD1779	Approved
0.5865	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7078	Approved
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.581	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5360	Phase 3
0.5789	Remote Similarity	NPD4159	Approved
0.5789	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4632	Approved
0.5776	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5777	Approved
0.5769	Remote Similarity	NPD6695	Phase 3
0.5755	Remote Similarity	NPD8308	Discontinued
0.5739	Remote Similarity	NPD7632	Discontinued
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6123	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5701	Remote Similarity	NPD7750	Discontinued
0.5692	Remote Similarity	NPD6033	Approved
0.5686	Remote Similarity	NPD7645	Phase 2
0.567	Remote Similarity	NPD4789	Approved
0.5664	Remote Similarity	NPD7919	Phase 3
0.5664	Remote Similarity	NPD7920	Phase 3
0.5631	Remote Similarity	NPD4748	Discontinued
0.563	Remote Similarity	NPD7320	Approved
0.563	Remote Similarity	NPD6899	Approved
0.563	Remote Similarity	NPD6881	Approved
0.562	Remote Similarity	NPD8130	Phase 1
0.562	Remote Similarity	NPD6650	Approved
0.562	Remote Similarity	NPD6649	Approved
0.5614	Remote Similarity	NPD8088	Phase 1

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