NPASS Compound

Structure

NPC36372 OpenBabel07101718302D 45 49 0 0 1 0 0 0 0 0999 V2000 4.2727 -0.8626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5599 0.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8396 3.6848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9621 0.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6423 1.6714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 3.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1998 1.9906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2216 1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6942 -0.5195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0961 0.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8281 -0.0195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2301 1.4805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5602 0.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8281 2.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5817 0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5088 2.9417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9126 0.8316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5602 -0.0195 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6942 1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6942 2.4805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9621 1.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4869 3.1496 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8937 4.0631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8882 3.9586 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0961 2.9805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8281 0.9805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2301 2.4805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9621 2.4805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.4262 -0.5195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5602 2.9805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3937 4.9292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5573 4.7017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9621 3.4805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 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 18 1 0 0 0 0 2 18 1 0 0 0 0 6 43 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 33 1 0 0 0 0 13 34 1 0 0 0 0 14 44 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 35 1 0 0 0 0 17 24 1 0 0 0 0 17 45 1 0 0 0 0 18 20 1 0 0 0 0 19 3 1 1 0 0 0 19 26 1 0 0 0 0 20 8 1 1 0 0 0 21 36 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 37 1 6 0 0 0 24 27 1 0 0 0 0 24 43 1 1 0 0 0 25 33 1 1 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 34 1 1 0 0 0 27 30 1 0 0 0 0 27 38 1 6 0 0 0 28 29 1 0 0 0 0 28 39 1 1 0 0 0 29 31 1 0 0 0 0 29 40 1 1 0 0 0 30 32 1 0 0 0 0 30 41 1 1 0 0 0 31 34 1 1 0 0 0 31 35 1 0 0 0 0 32 44 1 6 0 0 0 32 45 1 0 0 0 0 33 4 1 1 0 0 0 34 5 1 1 0 0 0 35 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.43
Volume:	659.036
LogP:	3.612
LogD:	3.688
LogS:	-3.46
# Rotatable Bonds:	10
TPSA:	169.3
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.675
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
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:	-5.404
MDCK Permeability:	5.5107044317992404e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.184
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	91.17166900634766%
Volume Distribution (VD):	0.392
Pgp-substrate:	5.636059761047363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	1.414
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.585
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.888
Carcinogencity:	0.035
Eye Corrosion:	0.02
Eye Irritation:	0.02
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC36372

Natural Product ID:	NPC36372
*Common Name:**	Certonardoside P1
IUPAC Name:	(3S,5S,6S,8S,9R,10S,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-[2-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxyethyl]-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15,16-pentol
Synonyms:	Certonardoside P1
Standard InCHIKey:	NRTSAVOORBOQBR-CQPGGYOESA-N
Standard InCHI:	InChI=1S/C35H62O10/c1-18(2)20(11-14-44-32-30(41)27(38)24(43-6)17-45-32)8-7-19(3)26-28(39)29(40)31-34(26,5)13-10-25-33(4)12-9-21(36)15-22(33)23(37)16-35(25,31)42/h18-32,36-42H,7-17H2,1-6H3/t19-,20-,21+,22-,23+,24-,25-,26+,27+,28-,29-,30-,31-,32-,33+,34-,35+/m1/s1
SMILES:	CO[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)OCC[C@H](C(C)C)CC[C@H]([C@H]1[C@@H](O)[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503163
PubChem CID:	11354212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.87	ug ml-1	PMID[471266]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.89	ug ml-1	PMID[471266]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.26	ug ml-1	PMID[471266]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.35	ug ml-1	PMID[471266]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	2.17	ug ml-1	PMID[471266]

☑ 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 NPC36372 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	538
0.1-0.2	4867
0.2-0.3	12729
0.3-0.4	11133
0.4-0.5	5564
0.5-0.6	3839
0.6-0.7	2584
0.7-0.8	1049
0.8-0.85	188
0.85-0.9	156
0.9-0.95	37
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC277774
0.9882	High Similarity	NPC279329
0.977	High Similarity	NPC309866
0.9767	High Similarity	NPC293609
0.9765	High Similarity	NPC102725
0.9659	High Similarity	NPC92196
0.9655	High Similarity	NPC311246
0.9655	High Similarity	NPC167644
0.9651	High Similarity	NPC223143
0.9647	High Similarity	NPC281004
0.9551	High Similarity	NPC473287
0.9545	High Similarity	NPC113500
0.9545	High Similarity	NPC473503
0.9545	High Similarity	NPC477224
0.9545	High Similarity	NPC3538
0.954	High Similarity	NPC204881
0.954	High Similarity	NPC473830
0.9535	High Similarity	NPC473472
0.9529	High Similarity	NPC43912
0.9529	High Similarity	NPC140446
0.9438	High Similarity	NPC473067
0.9438	High Similarity	NPC473065
0.9438	High Similarity	NPC473064
0.9438	High Similarity	NPC469710
0.9425	High Similarity	NPC65550
0.9425	High Similarity	NPC473542
0.9326	High Similarity	NPC24960
0.9326	High Similarity	NPC252253
0.9326	High Similarity	NPC175
0.9326	High Similarity	NPC473774
0.9326	High Similarity	NPC45959
0.9326	High Similarity	NPC475325
0.9318	High Similarity	NPC476668
0.9318	High Similarity	NPC5632
0.9318	High Similarity	NPC149966
0.9318	High Similarity	NPC473637
0.931	High Similarity	NPC82955
0.931	High Similarity	NPC131466
0.9294	High Similarity	NPC290612
0.9231	High Similarity	NPC470028
0.9231	High Similarity	NPC477223
0.9231	High Similarity	NPC233649
0.9231	High Similarity	NPC477222
0.9222	High Similarity	NPC474399
0.9213	High Similarity	NPC144790
0.9213	High Similarity	NPC149400
0.9213	High Similarity	NPC476669
0.9213	High Similarity	NPC137004
0.9213	High Similarity	NPC88962
0.9213	High Similarity	NPC172838
0.9213	High Similarity	NPC473726
0.913	High Similarity	NPC473638
0.9121	High Similarity	NPC139271
0.9121	High Similarity	NPC142264
0.9121	High Similarity	NPC476510
0.9121	High Similarity	NPC296936
0.9121	High Similarity	NPC304011
0.9111	High Similarity	NPC253268
0.9111	High Similarity	NPC475436
0.9111	High Similarity	NPC179859
0.9111	High Similarity	NPC131693
0.9111	High Similarity	NPC291547
0.9111	High Similarity	NPC312678
0.9111	High Similarity	NPC174024
0.9111	High Similarity	NPC473851
0.9101	High Similarity	NPC307167
0.9101	High Similarity	NPC210759
0.9101	High Similarity	NPC59006
0.9101	High Similarity	NPC229801
0.9091	High Similarity	NPC20822
0.908	High Similarity	NPC472396
0.9022	High Similarity	NPC274200
0.9011	High Similarity	NPC477494
0.9	High Similarity	NPC234352
0.9	High Similarity	NPC48339
0.9	High Similarity	NPC250393
0.9	High Similarity	NPC297348
0.9	High Similarity	NPC477451
0.9	High Similarity	NPC177834
0.9	High Similarity	NPC141769
0.9	High Similarity	NPC477547
0.9	High Similarity	NPC325828
0.9	High Similarity	NPC249204
0.8936	High Similarity	NPC476839
0.8936	High Similarity	NPC475574
0.8936	High Similarity	NPC476838
0.8936	High Similarity	NPC477225
0.8925	High Similarity	NPC473616
0.8913	High Similarity	NPC121453
0.8901	High Similarity	NPC264101
0.8901	High Similarity	NPC471464
0.8901	High Similarity	NPC30687
0.8901	High Similarity	NPC151214
0.8901	High Similarity	NPC291203
0.8901	High Similarity	NPC191915
0.8901	High Similarity	NPC294686
0.8901	High Similarity	NPC305418
0.8901	High Similarity	NPC217205
0.8901	High Similarity	NPC222731
0.8876	High Similarity	NPC228059
0.8842	High Similarity	NPC114700
0.8842	High Similarity	NPC470029
0.8842	High Similarity	NPC134967
0.8842	High Similarity	NPC310138
0.8817	High Similarity	NPC307534
0.8817	High Similarity	NPC476112
0.8817	High Similarity	NPC470591
0.8817	High Similarity	NPC475207
0.8817	High Similarity	NPC210157
0.8804	High Similarity	NPC473727
0.8804	High Similarity	NPC94582
0.8804	High Similarity	NPC107962
0.8804	High Similarity	NPC57964
0.8804	High Similarity	NPC206003
0.8804	High Similarity	NPC211354
0.8804	High Similarity	NPC6295
0.8804	High Similarity	NPC107188
0.8804	High Similarity	NPC473610
0.8804	High Similarity	NPC475351
0.8804	High Similarity	NPC19400
0.875	High Similarity	NPC471240
0.8737	High Similarity	NPC476512
0.8737	High Similarity	NPC477172
0.8737	High Similarity	NPC472081
0.8737	High Similarity	NPC108227
0.8736	High Similarity	NPC474156
0.8723	High Similarity	NPC291548
0.8723	High Similarity	NPC473518
0.871	High Similarity	NPC84111
0.871	High Similarity	NPC132080
0.871	High Similarity	NPC97700
0.871	High Similarity	NPC203434
0.871	High Similarity	NPC232037
0.871	High Similarity	NPC470863
0.871	High Similarity	NPC252056
0.871	High Similarity	NPC103616
0.871	High Similarity	NPC98018
0.871	High Similarity	NPC475643
0.871	High Similarity	NPC470866
0.871	High Similarity	NPC470865
0.871	High Similarity	NPC195297
0.871	High Similarity	NPC128572
0.871	High Similarity	NPC473601
0.871	High Similarity	NPC475625
0.871	High Similarity	NPC472989
0.871	High Similarity	NPC287483
0.871	High Similarity	NPC160426
0.871	High Similarity	NPC237071
0.871	High Similarity	NPC156377
0.871	High Similarity	NPC238796
0.871	High Similarity	NPC284104
0.871	High Similarity	NPC470864
0.871	High Similarity	NPC30856
0.871	High Similarity	NPC184617
0.871	High Similarity	NPC116756
0.866	High Similarity	NPC475521
0.8652	High Similarity	NPC161928
0.8652	High Similarity	NPC210658
0.8636	High Similarity	NPC232044
0.8636	High Similarity	NPC273290
0.8632	High Similarity	NPC470030
0.8632	High Similarity	NPC41843
0.8621	High Similarity	NPC241959
0.8617	High Similarity	NPC470861
0.8617	High Similarity	NPC303069
0.8617	High Similarity	NPC51520
0.8617	High Similarity	NPC470862
0.8617	High Similarity	NPC83137
0.8617	High Similarity	NPC115165
0.8617	High Similarity	NPC232611
0.8557	High Similarity	NPC97260
0.8557	High Similarity	NPC476837
0.8557	High Similarity	NPC139181
0.8556	High Similarity	NPC128475
0.8542	High Similarity	NPC31346
0.8523	High Similarity	NPC227260
0.8506	High Similarity	NPC470611
0.8506	High Similarity	NPC296734
0.8471	Intermediate Similarity	NPC177343
0.8469	Intermediate Similarity	NPC312774
0.8438	Intermediate Similarity	NPC20028
0.8421	Intermediate Similarity	NPC76486
0.8404	Intermediate Similarity	NPC215570
0.84	Intermediate Similarity	NPC475634
0.8387	Intermediate Similarity	NPC224003
0.8387	Intermediate Similarity	NPC171741
0.8387	Intermediate Similarity	NPC470623
0.8387	Intermediate Similarity	NPC18724
0.8387	Intermediate Similarity	NPC323231
0.8367	Intermediate Similarity	NPC34562
0.8353	Intermediate Similarity	NPC185915
0.8351	Intermediate Similarity	NPC472023
0.8351	Intermediate Similarity	NPC47566
0.8351	Intermediate Similarity	NPC129372
0.8351	Intermediate Similarity	NPC4831
0.8351	Intermediate Similarity	NPC160734
0.8351	Intermediate Similarity	NPC309425
0.8351	Intermediate Similarity	NPC88000
0.8333	Intermediate Similarity	NPC292775
0.8317	Intermediate Similarity	NPC474573

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 NPC36372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	533
0.1-0.2	4532
0.2-0.3	2833
0.3-0.4	650
0.4-0.5	288
0.5-0.6	246
0.6-0.7	49
0.7-0.8	17
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
0.9	High Similarity	NPD8171	Discontinued
0.8276	Intermediate Similarity	NPD6928	Phase 2
0.81	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7327	Approved
0.7545	Intermediate Similarity	NPD7328	Approved
0.7529	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7477	Intermediate Similarity	NPD7516	Approved
0.7411	Intermediate Similarity	NPD8294	Approved
0.7411	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8033	Approved
0.7339	Intermediate Similarity	NPD8133	Approved
0.73	Intermediate Similarity	NPD7991	Discontinued
0.7191	Intermediate Similarity	NPD1811	Approved
0.7191	Intermediate Similarity	NPD1810	Approved
0.6949	Remote Similarity	NPD7507	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.6917	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD7503	Approved
0.6854	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2687	Approved
0.6854	Remote Similarity	NPD4787	Phase 1
0.6854	Remote Similarity	NPD2254	Approved
0.6854	Remote Similarity	NPD2686	Approved
0.6818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6940	Discontinued
0.6744	Remote Similarity	NPD371	Approved
0.6727	Remote Similarity	NPD8174	Phase 2
0.6702	Remote Similarity	NPD6115	Approved
0.6702	Remote Similarity	NPD6118	Approved
0.6702	Remote Similarity	NPD6114	Approved
0.6702	Remote Similarity	NPD6697	Approved
0.6701	Remote Similarity	NPD3669	Approved
0.6701	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7736	Approved
0.6596	Remote Similarity	NPD6116	Phase 1
0.6555	Remote Similarity	NPD6370	Approved
0.6552	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6117	Approved
0.6475	Remote Similarity	NPD8293	Discontinued
0.6392	Remote Similarity	NPD7525	Registered
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6277	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8328	Phase 3
0.622	Remote Similarity	NPD8449	Approved
0.6211	Remote Similarity	NPD3703	Phase 2
0.6211	Remote Similarity	NPD3702	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.6179	Remote Similarity	NPD7492	Approved
0.6172	Remote Similarity	NPD8450	Suspended
0.6148	Remote Similarity	NPD5988	Approved
0.614	Remote Similarity	NPD6686	Approved
0.6129	Remote Similarity	NPD6616	Approved
0.6129	Remote Similarity	NPD4244	Approved
0.6129	Remote Similarity	NPD4245	Approved
0.6117	Remote Similarity	NPD7524	Approved
0.6116	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD6067	Discontinued
0.608	Remote Similarity	NPD7078	Approved
0.6068	Remote Similarity	NPD8297	Approved
0.6068	Remote Similarity	NPD6882	Approved
0.6036	Remote Similarity	NPD1700	Approved
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3698	Phase 2
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1779	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD1780	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5360	Phase 3
0.5914	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6033	Approved
0.5895	Remote Similarity	NPD5777	Approved
0.5893	Remote Similarity	NPD4159	Approved
0.5882	Remote Similarity	NPD6695	Phase 3
0.5882	Remote Similarity	NPD4632	Approved
0.587	Remote Similarity	NPD7625	Phase 1
0.5865	Remote Similarity	NPD8308	Discontinued
0.5843	Remote Similarity	NPD6123	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.5826	Remote Similarity	NPD5739	Approved
0.5826	Remote Similarity	NPD7128	Approved
0.5826	Remote Similarity	NPD6402	Approved
0.5826	Remote Similarity	NPD6675	Approved
0.5812	Remote Similarity	NPD6373	Approved
0.5812	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD7750	Discontinued
0.58	Remote Similarity	NPD7645	Phase 2
0.5794	Remote Similarity	NPD6700	Approved
0.5794	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4789	Approved
0.5763	Remote Similarity	NPD4634	Approved
0.5743	Remote Similarity	NPD4748	Discontinued
0.5741	Remote Similarity	NPD6702	Approved
0.5741	Remote Similarity	NPD6703	Approved
0.5726	Remote Similarity	NPD6899	Approved
0.5726	Remote Similarity	NPD6881	Approved
0.5726	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6650	Approved
0.5664	Remote Similarity	NPD8418	Phase 2
0.566	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD2269	Approved
0.5641	Remote Similarity	NPD5697	Approved
0.5641	Remote Similarity	NPD5701	Approved
0.563	Remote Similarity	NPD6883	Approved
0.563	Remote Similarity	NPD7102	Approved
0.563	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD4755	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