NPASS Compound

Structure

NPC223143 OpenBabel07101719252D 45 49 0 0 1 0 0 0 0 0999 V2000 -3.3457 3.7157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 2.5568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9126 -0.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0351 2.3727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7152 1.1817 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 -4.2727 0.8626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1690 1.8727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7671 3.3727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3030 1.3727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9011 2.8727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9011 -0.1273 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 -3.6547 2.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 -0.0885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9855 2.0215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0351 0.3727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0351 1.3727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6331 2.8727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7671 0.3727 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 -5.5599 -0.2964 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1690 -0.1273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7671 1.3727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6331 1.8727 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 -5.9666 -1.2100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9611 -1.1054 0.0000 C 0 0 1 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 -0.9781 -0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9011 1.8727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3030 0.3727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4992 3.3727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6331 -0.1273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4992 1.3727 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 -5.4666 -2.0760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6303 -1.8486 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 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 17 1 0 0 0 0 2 17 1 0 0 0 0 6 43 1 0 0 0 0 7 8 1 0 0 0 0 7 18 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 22 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 35 1 0 0 0 0 13 34 1 0 0 0 0 14 44 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 16 45 1 0 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 18 25 1 0 0 0 0 19 8 1 1 0 0 0 20 15 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 34 1 1 0 0 0 22 28 1 0 0 0 0 22 36 1 1 0 0 0 23 27 1 0 0 0 0 23 37 1 6 0 0 0 24 29 1 0 0 0 0 24 43 1 1 0 0 0 25 30 1 0 0 0 0 25 35 1 1 0 0 0 26 31 1 0 0 0 0 26 35 1 1 0 0 0 27 28 1 0 0 0 0 27 34 1 1 0 0 0 28 38 1 1 0 0 0 29 32 1 0 0 0 0 29 39 1 6 0 0 0 30 31 1 0 0 0 0 30 40 1 1 0 0 0 31 41 1 1 0 0 0 32 33 1 0 0 0 0 32 42 1 1 0 0 0 33 44 1 6 0 0 0 33 45 1 0 0 0 0 34 4 1 1 0 0 0 35 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.17
Volume:	488.462
LogP:	5.771
LogD:	4.002
LogS:	-4.557
# Rotatable Bonds:	1
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	5.379
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.361
MDCK Permeability:	9.974121894629207e-06
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.668
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.83637237548828%
Volume Distribution (VD):	0.214
Pgp-substrate:	0.7819233536720276%

ADMET: Metabolism

CYP1A2-inhibitor:	0.642
CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.865
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.543
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.198
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.745

ADMET: Excretion

Clearance (CL):	10.429
Half-life (T1/2):	0.577

ADMET: Toxicity

hERG Blockers:	0.49
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.974
Carcinogencity:	0.319
Eye Corrosion:	0.003
Eye Irritation:	0.693
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC223143

Natural Product ID:	NPC223143
*Common Name:**	Certonardoside J2
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,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-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,6,15,16-pentol
Synonyms:	Certonardoside J2
Standard InCHIKey:	NTIYFKBUVFNOIK-XCIXNCJBSA-N
Standard InCHI:	InChI=1S/C35H62O10/c1-17(2)19(11-14-44-33-32(42)29(39)24(43-6)16-45-33)8-7-18(3)25-30(40)31(41)26-20-15-23(37)27-28(38)22(36)10-13-34(27,4)21(20)9-12-35(25,26)5/h17-33,36-42H,7-16H2,1-6H3/t18-,19-,20-,21+,22+,23+,24-,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35-/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1[C@H]([C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)O)CCO[C@H]1[C@@H]([C@H]([C@@H](CO1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499765
PubChem CID:	11377220
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	=	3.41	ug ml-1	PMID[456423]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.29	ug ml-1	PMID[456423]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	2.36	ug ml-1	PMID[456423]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.53	ug ml-1	PMID[456423]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	8.2	ug ml-1	PMID[456423]

☑ 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 NPC223143 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	530
0.1-0.2	4779
0.2-0.3	12966
0.3-0.4	11113
0.4-0.5	5547
0.5-0.6	3726
0.6-0.7	2631
0.7-0.8	1022
0.8-0.85	175
0.85-0.9	162
0.9-0.95	35
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC102725
0.9881	High Similarity	NPC473472
0.9767	High Similarity	NPC277774
0.9762	High Similarity	NPC281004
0.9655	High Similarity	NPC475325
0.9651	High Similarity	NPC36372
0.9651	High Similarity	NPC5632
0.9651	High Similarity	NPC293609
0.9651	High Similarity	NPC149966
0.9545	High Similarity	NPC92196
0.954	High Similarity	NPC476669
0.9535	High Similarity	NPC279329
0.9535	High Similarity	NPC473542
0.9535	High Similarity	NPC65550
0.9438	High Similarity	NPC473287
0.9432	High Similarity	NPC309866
0.9432	High Similarity	NPC113500
0.9432	High Similarity	NPC477224
0.9432	High Similarity	NPC3538
0.9425	High Similarity	NPC473637
0.9425	High Similarity	NPC204881
0.9425	High Similarity	NPC476668
0.9425	High Similarity	NPC473830
0.9419	High Similarity	NPC20822
0.9412	High Similarity	NPC43912
0.9412	High Similarity	NPC140446
0.9326	High Similarity	NPC473065
0.9326	High Similarity	NPC473064
0.9326	High Similarity	NPC473067
0.9318	High Similarity	NPC311246
0.9318	High Similarity	NPC88962
0.9318	High Similarity	NPC149400
0.9318	High Similarity	NPC473726
0.9318	High Similarity	NPC144790
0.9318	High Similarity	NPC167644
0.9318	High Similarity	NPC172838
0.9318	High Similarity	NPC137004
0.9222	High Similarity	NPC121453
0.9213	High Similarity	NPC473851
0.9213	High Similarity	NPC473774
0.9213	High Similarity	NPC175
0.9213	High Similarity	NPC473503
0.9213	High Similarity	NPC475436
0.9213	High Similarity	NPC253268
0.9213	High Similarity	NPC312678
0.9213	High Similarity	NPC131693
0.9213	High Similarity	NPC174024
0.9213	High Similarity	NPC24960
0.9213	High Similarity	NPC291547
0.9213	High Similarity	NPC45959
0.9213	High Similarity	NPC222731
0.9213	High Similarity	NPC252253
0.9213	High Similarity	NPC179859
0.9213	High Similarity	NPC294686
0.9195	High Similarity	NPC131466
0.9195	High Similarity	NPC82955
0.9176	High Similarity	NPC290612
0.9121	High Similarity	NPC477222
0.9121	High Similarity	NPC470028
0.9121	High Similarity	NPC233649
0.9121	High Similarity	NPC477223
0.9111	High Similarity	NPC469710
0.9111	High Similarity	NPC474399
0.9101	High Similarity	NPC249204
0.9101	High Similarity	NPC477547
0.9101	High Similarity	NPC234352
0.9101	High Similarity	NPC48339
0.9101	High Similarity	NPC297348
0.9101	High Similarity	NPC477451
0.9101	High Similarity	NPC325828
0.9101	High Similarity	NPC250393
0.9101	High Similarity	NPC177834
0.9101	High Similarity	NPC141769
0.907	High Similarity	NPC471240
0.9022	High Similarity	NPC291548
0.9022	High Similarity	NPC473638
0.9022	High Similarity	NPC473518
0.9011	High Similarity	NPC142264
0.9011	High Similarity	NPC476510
0.9011	High Similarity	NPC296936
0.9011	High Similarity	NPC195297
0.9011	High Similarity	NPC473601
0.9011	High Similarity	NPC139271
0.9011	High Similarity	NPC304011
0.9	High Similarity	NPC471464
0.9	High Similarity	NPC217205
0.9	High Similarity	NPC291203
0.9	High Similarity	NPC264101
0.8989	High Similarity	NPC229801
0.8989	High Similarity	NPC307167
0.8989	High Similarity	NPC59006
0.8989	High Similarity	NPC210759
0.8953	High Similarity	NPC232044
0.8953	High Similarity	NPC273290
0.8913	High Similarity	NPC475207
0.8913	High Similarity	NPC51520
0.8913	High Similarity	NPC303069
0.8913	High Similarity	NPC470862
0.8913	High Similarity	NPC470861
0.8913	High Similarity	NPC307534
0.8913	High Similarity	NPC83137
0.8913	High Similarity	NPC274200
0.8913	High Similarity	NPC232611
0.8913	High Similarity	NPC115165
0.8913	High Similarity	NPC470591
0.8913	High Similarity	NPC210157
0.8913	High Similarity	NPC476112
0.8901	High Similarity	NPC57964
0.8901	High Similarity	NPC473727
0.8901	High Similarity	NPC94582
0.8901	High Similarity	NPC206003
0.8901	High Similarity	NPC473610
0.8901	High Similarity	NPC477494
0.8901	High Similarity	NPC107188
0.8901	High Similarity	NPC475351
0.8901	High Similarity	NPC107962
0.8901	High Similarity	NPC19400
0.8901	High Similarity	NPC211354
0.8901	High Similarity	NPC6295
0.8837	High Similarity	NPC227260
0.883	High Similarity	NPC476839
0.883	High Similarity	NPC31346
0.883	High Similarity	NPC477225
0.883	High Similarity	NPC476838
0.8817	High Similarity	NPC473616
0.8804	High Similarity	NPC287483
0.8804	High Similarity	NPC475643
0.8804	High Similarity	NPC128572
0.8804	High Similarity	NPC84111
0.8804	High Similarity	NPC103616
0.8804	High Similarity	NPC116756
0.8804	High Similarity	NPC470865
0.8804	High Similarity	NPC232037
0.8804	High Similarity	NPC132080
0.8804	High Similarity	NPC475625
0.8804	High Similarity	NPC284104
0.8804	High Similarity	NPC470863
0.8804	High Similarity	NPC470866
0.8804	High Similarity	NPC160426
0.8804	High Similarity	NPC30856
0.8804	High Similarity	NPC98018
0.8804	High Similarity	NPC97700
0.8804	High Similarity	NPC184617
0.8804	High Similarity	NPC470864
0.8791	High Similarity	NPC191915
0.8791	High Similarity	NPC151214
0.8791	High Similarity	NPC30687
0.8791	High Similarity	NPC305418
0.8764	High Similarity	NPC228059
0.875	High Similarity	NPC472396
0.875	High Similarity	NPC312774
0.8737	High Similarity	NPC114700
0.8737	High Similarity	NPC310138
0.8737	High Similarity	NPC134967
0.8737	High Similarity	NPC470029
0.8723	High Similarity	NPC41843
0.8652	High Similarity	NPC128475
0.8632	High Similarity	NPC477172
0.8632	High Similarity	NPC475574
0.8632	High Similarity	NPC472081
0.8632	High Similarity	NPC108227
0.8632	High Similarity	NPC476512
0.8621	High Similarity	NPC474156
0.8605	High Similarity	NPC296734
0.8605	High Similarity	NPC470611
0.8602	High Similarity	NPC203434
0.8602	High Similarity	NPC252056
0.8602	High Similarity	NPC238796
0.8602	High Similarity	NPC472989
0.8602	High Similarity	NPC156377
0.8602	High Similarity	NPC237071
0.8557	High Similarity	NPC475521
0.8539	High Similarity	NPC161928
0.8539	High Similarity	NPC210658
0.8526	High Similarity	NPC470030
0.8526	High Similarity	NPC20028
0.8511	High Similarity	NPC76486
0.8506	High Similarity	NPC241959
0.8454	Intermediate Similarity	NPC139181
0.8454	Intermediate Similarity	NPC97260
0.8454	Intermediate Similarity	NPC476837
0.8421	Intermediate Similarity	NPC292775
0.8372	Intermediate Similarity	NPC7479
0.8372	Intermediate Similarity	NPC257296
0.8372	Intermediate Similarity	NPC248944
0.8367	Intermediate Similarity	NPC475365
0.8353	Intermediate Similarity	NPC177343
0.8351	Intermediate Similarity	NPC310031
0.8351	Intermediate Similarity	NPC80191
0.8333	Intermediate Similarity	NPC7341
0.8333	Intermediate Similarity	NPC471247
0.8333	Intermediate Similarity	NPC473200
0.8333	Intermediate Similarity	NPC91497
0.8316	Intermediate Similarity	NPC472273
0.8298	Intermediate Similarity	NPC215570
0.828	Intermediate Similarity	NPC171741
0.828	Intermediate Similarity	NPC182740
0.828	Intermediate Similarity	NPC224003
0.828	Intermediate Similarity	NPC18724
0.828	Intermediate Similarity	NPC122083

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 NPC223143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	526
0.1-0.2	4479
0.2-0.3	2897
0.3-0.4	639
0.4-0.5	309
0.5-0.6	231
0.6-0.7	51
0.7-0.8	15
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD8171	Discontinued
0.8372	Intermediate Similarity	NPD6928	Phase 2
0.8182	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7516	Approved
0.7374	Intermediate Similarity	NPD7991	Discontinued
0.7321	Intermediate Similarity	NPD8377	Approved
0.7321	Intermediate Similarity	NPD8294	Approved
0.7297	Intermediate Similarity	NPD7327	Approved
0.7297	Intermediate Similarity	NPD7328	Approved
0.7257	Intermediate Similarity	NPD8296	Approved
0.7257	Intermediate Similarity	NPD8380	Approved
0.7257	Intermediate Similarity	NPD8335	Approved
0.7257	Intermediate Similarity	NPD8379	Approved
0.7257	Intermediate Similarity	NPD8033	Approved
0.7257	Intermediate Similarity	NPD8378	Approved
0.7248	Intermediate Similarity	NPD8133	Approved
0.7079	Intermediate Similarity	NPD1810	Approved
0.7079	Intermediate Similarity	NPD1811	Approved
0.7037	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.6932	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7507	Approved
0.6814	Remote Similarity	NPD6940	Discontinued
0.681	Remote Similarity	NPD7503	Approved
0.6789	Remote Similarity	NPD8174	Phase 2
0.6774	Remote Similarity	NPD6118	Approved
0.6774	Remote Similarity	NPD6114	Approved
0.6774	Remote Similarity	NPD6115	Approved
0.6774	Remote Similarity	NPD6697	Approved
0.6742	Remote Similarity	NPD2687	Approved
0.6742	Remote Similarity	NPD2254	Approved
0.6742	Remote Similarity	NPD4787	Phase 1
0.6742	Remote Similarity	NPD2686	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6628	Remote Similarity	NPD371	Approved
0.6612	Remote Similarity	NPD7736	Approved
0.6609	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3669	Approved
0.6559	Remote Similarity	NPD6117	Approved
0.6471	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6344	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD6059	Approved
0.6289	Remote Similarity	NPD7525	Registered
0.6281	Remote Similarity	NPD8328	Phase 3
0.6277	Remote Similarity	NPD3703	Phase 2
0.627	Remote Similarity	NPD8449	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD8035	Phase 2
0.622	Remote Similarity	NPD8450	Suspended
0.6196	Remote Similarity	NPD4245	Approved
0.6196	Remote Similarity	NPD4244	Approved
0.6195	Remote Similarity	NPD6686	Approved
0.6148	Remote Similarity	NPD6067	Discontinued
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6105	Remote Similarity	NPD3702	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6087	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3698	Phase 2
0.6087	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5988	Approved
0.6055	Remote Similarity	NPD7638	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.6033	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7078	Approved
0.5983	Remote Similarity	NPD6882	Approved
0.5983	Remote Similarity	NPD8297	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5777	Approved
0.5946	Remote Similarity	NPD1700	Approved
0.5929	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD8308	Discontinued
0.5917	Remote Similarity	NPD6009	Approved
0.5913	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD7625	Phase 1
0.5909	Remote Similarity	NPD6123	Approved
0.59	Remote Similarity	NPD1779	Approved
0.59	Remote Similarity	NPD1780	Approved
0.5893	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD7645	Phase 2
0.5851	Remote Similarity	NPD4789	Approved
0.5849	Remote Similarity	NPD6700	Approved
0.5849	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6033	Approved
0.5806	Remote Similarity	NPD5360	Phase 3
0.5806	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4159	Approved
0.5798	Remote Similarity	NPD4632	Approved
0.5794	Remote Similarity	NPD6703	Approved
0.5794	Remote Similarity	NPD6702	Approved
0.5739	Remote Similarity	NPD6402	Approved
0.5739	Remote Similarity	NPD5739	Approved
0.5739	Remote Similarity	NPD6675	Approved
0.5739	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6372	Approved
0.5726	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8418	Phase 2
0.5714	Remote Similarity	NPD2269	Approved
0.5678	Remote Similarity	NPD4634	Approved
0.5652	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD889	Approved
0.5647	Remote Similarity	NPD895	Approved
0.5647	Remote Similarity	NPD891	Phase 3
0.5647	Remote Similarity	NPD892	Phase 3
0.5647	Remote Similarity	NPD894	Approved
0.5647	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD888	Phase 3
0.5647	Remote Similarity	NPD893	Approved
0.5647	Remote Similarity	NPD887	Approved
0.5644	Remote Similarity	NPD4748	Discontinued
0.5641	Remote Similarity	NPD6899	Approved
0.5641	Remote Similarity	NPD6881	Approved
0.5641	Remote Similarity	NPD7320	Approved
0.5632	Remote Similarity	NPD2267	Suspended
0.5631	Remote Similarity	NPD6695	Phase 3
0.563	Remote Similarity	NPD8130	Phase 1
0.563	Remote Similarity	NPD6650	Approved
0.563	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD6081	Approved
0.5612	Remote Similarity	NPD6942	Approved
0.5612	Remote Similarity	NPD7339	Approved
0.56	Remote Similarity	NPD3671	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