NPASS Compound

Structure

NPC20822 OpenBabel07101718272D 41 45 0 0 1 0 0 0 0 0999 V2000 -1.0563 -2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6962 -0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0006 0.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6807 -1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1346 -0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7326 1.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2685 -0.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8666 0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8666 -2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9321 -3.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 -1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0006 -1.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0006 -0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5254 -2.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5987 0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7326 -1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9266 -3.4360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5909 -2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1346 -2.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7326 -0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5987 -0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8666 -0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2685 -1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7045 2.5823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4647 1.0422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5987 -2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5958 -4.1791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4647 -0.9578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 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 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 32 1 0 0 0 0 11 31 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 33 1 0 0 0 0 15 23 1 0 0 0 0 16 3 1 1 0 0 0 16 19 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 31 1 6 0 0 0 19 32 1 6 0 0 0 20 27 1 0 0 0 0 20 34 1 6 0 0 0 21 26 1 0 0 0 0 21 35 1 1 0 0 0 22 25 1 0 0 0 0 22 36 1 6 0 0 0 23 7 1 1 0 0 0 23 40 1 0 0 0 0 24 14 1 6 0 0 0 24 28 1 0 0 0 0 24 41 1 0 0 0 0 25 32 1 6 0 0 0 26 27 1 0 0 0 0 26 31 1 6 0 0 0 27 37 1 6 0 0 0 28 29 1 0 0 0 0 28 38 1 6 0 0 0 29 30 1 0 0 0 0 29 39 1 1 0 0 0 30 40 1 6 0 0 0 30 41 1 0 0 0 0 31 4 1 6 0 0 0 32 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	255.515
LogP:	1.179
LogD:	1.784
LogS:	-3.05
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	4.519
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.636
MDCK Permeability:	6.88868312863633e-05
Pgp-inhibitor:	0.549
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.661
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	77.81879425048828%
Volume Distribution (VD):	1.178
Pgp-substrate:	30.873802185058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.71
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.255
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.108
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	11.741
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.437
AMES Toxicity:	0.265
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.469
Carcinogencity:	0.806
Eye Corrosion:	0.815
Eye Irritation:	0.714
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC20822

Natural Product ID:	NPC20822
*Common Name:**	Certonardoside H4
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,5S)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-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-tetrol
Synonyms:	Certonardoside H4
Standard InCHIKey:	QCMLKBFJNBTXOO-BOLZVVRMSA-N
Standard InCHI:	InChI=1S/C32H56O9/c1-15(2)23(40-30-29(39)28(38)24(14-33)41-30)7-6-16(3)19-13-22(36)25-17-12-21(35)26-27(37)20(34)9-11-31(26,4)18(17)8-10-32(19,25)5/h15-30,33-39H,6-14H2,1-5H3/t16-,17-,18+,19-,20+,21+,22-,23+,24-,25-,26+,27+,28+,29-,30-,31-,32-/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1C[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[C@H]1[C@@H]([C@H]([C@@H](CO)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446038
PubChem CID:	23251484
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
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	>	30.0	ug ml-1	PMID[458406]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[458406]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	8.3	ug ml-1	PMID[458406]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[458406]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[458406]

☑ 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 NPC20822 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	494
0.1-0.2	4561
0.2-0.3	13179
0.3-0.4	10798
0.4-0.5	5740
0.5-0.6	4199
0.6-0.7	2444
0.7-0.8	962
0.8-0.85	147
0.85-0.9	134
0.9-0.95	36
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC5632
0.9765	High Similarity	NPC149966
0.9647	High Similarity	NPC473542
0.954	High Similarity	NPC3538
0.954	High Similarity	NPC113500
0.954	High Similarity	NPC477224
0.9529	High Similarity	NPC473472
0.9425	High Similarity	NPC311246
0.9425	High Similarity	NPC149400
0.9425	High Similarity	NPC144790
0.9425	High Similarity	NPC167644
0.9425	High Similarity	NPC88962
0.9419	High Similarity	NPC223143
0.9412	High Similarity	NPC281004
0.9326	High Similarity	NPC121453
0.9318	High Similarity	NPC253268
0.9318	High Similarity	NPC174024
0.9318	High Similarity	NPC179859
0.9318	High Similarity	NPC222731
0.9318	High Similarity	NPC294686
0.9318	High Similarity	NPC312678
0.9318	High Similarity	NPC475436
0.9318	High Similarity	NPC175
0.9318	High Similarity	NPC473774
0.9318	High Similarity	NPC131693
0.9318	High Similarity	NPC45959
0.9318	High Similarity	NPC291547
0.9318	High Similarity	NPC473851
0.9318	High Similarity	NPC24960
0.9318	High Similarity	NPC252253
0.931	High Similarity	NPC293609
0.9302	High Similarity	NPC82955
0.9302	High Similarity	NPC102725
0.9222	High Similarity	NPC477222
0.9222	High Similarity	NPC477223
0.9213	High Similarity	NPC473067
0.9213	High Similarity	NPC473065
0.9213	High Similarity	NPC473064
0.9205	High Similarity	NPC177834
0.9205	High Similarity	NPC250393
0.9205	High Similarity	NPC141769
0.9205	High Similarity	NPC477451
0.9205	High Similarity	NPC297348
0.9205	High Similarity	NPC325828
0.9205	High Similarity	NPC476669
0.9205	High Similarity	NPC48339
0.9205	High Similarity	NPC249204
0.9205	High Similarity	NPC277774
0.9205	High Similarity	NPC234352
0.9205	High Similarity	NPC477547
0.9195	High Similarity	NPC65550
0.9195	High Similarity	NPC279329
0.9186	High Similarity	NPC128475
0.9157	High Similarity	NPC470611
0.9121	High Similarity	NPC473518
0.9121	High Similarity	NPC473638
0.9111	High Similarity	NPC139271
0.9111	High Similarity	NPC304011
0.9111	High Similarity	NPC473601
0.9111	High Similarity	NPC476510
0.9111	High Similarity	NPC142264
0.9111	High Similarity	NPC195297
0.9101	High Similarity	NPC217205
0.9101	High Similarity	NPC264101
0.9101	High Similarity	NPC471464
0.9101	High Similarity	NPC291203
0.9101	High Similarity	NPC475325
0.9091	High Similarity	NPC473830
0.9091	High Similarity	NPC476668
0.9091	High Similarity	NPC204881
0.9091	High Similarity	NPC473637
0.9091	High Similarity	NPC210759
0.9091	High Similarity	NPC229801
0.9091	High Similarity	NPC307167
0.9091	High Similarity	NPC36372
0.907	High Similarity	NPC161928
0.907	High Similarity	NPC140446
0.907	High Similarity	NPC210658
0.907	High Similarity	NPC43912
0.9059	High Similarity	NPC273290
0.9059	High Similarity	NPC232044
0.9011	High Similarity	NPC476112
0.9011	High Similarity	NPC51520
0.9011	High Similarity	NPC303069
0.9011	High Similarity	NPC475207
0.9011	High Similarity	NPC233649
0.9011	High Similarity	NPC83137
0.9011	High Similarity	NPC470862
0.9011	High Similarity	NPC232611
0.9011	High Similarity	NPC307534
0.9011	High Similarity	NPC470861
0.9011	High Similarity	NPC115165
0.9011	High Similarity	NPC470028
0.9	High Similarity	NPC473610
0.9	High Similarity	NPC474399
0.9	High Similarity	NPC19400
0.9	High Similarity	NPC206003
0.9	High Similarity	NPC211354
0.9	High Similarity	NPC475351
0.9	High Similarity	NPC107962
0.9	High Similarity	NPC473727
0.9	High Similarity	NPC107188
0.9	High Similarity	NPC92196
0.9	High Similarity	NPC6295
0.8989	High Similarity	NPC137004
0.8989	High Similarity	NPC473726
0.8989	High Similarity	NPC172838
0.8941	High Similarity	NPC227260
0.8925	High Similarity	NPC477225
0.8913	High Similarity	NPC473616
0.8913	High Similarity	NPC292775
0.8913	High Similarity	NPC291548
0.8901	High Similarity	NPC132080
0.8901	High Similarity	NPC284104
0.8901	High Similarity	NPC184617
0.8901	High Similarity	NPC287483
0.8901	High Similarity	NPC30856
0.8901	High Similarity	NPC475643
0.8901	High Similarity	NPC128572
0.8901	High Similarity	NPC84111
0.8901	High Similarity	NPC103616
0.8901	High Similarity	NPC116756
0.8901	High Similarity	NPC232037
0.8901	High Similarity	NPC470865
0.8901	High Similarity	NPC475625
0.8901	High Similarity	NPC470866
0.8901	High Similarity	NPC160426
0.8901	High Similarity	NPC98018
0.8901	High Similarity	NPC470864
0.8901	High Similarity	NPC470863
0.8901	High Similarity	NPC97700
0.8901	High Similarity	NPC473287
0.8889	High Similarity	NPC309866
0.8889	High Similarity	NPC305418
0.8889	High Similarity	NPC473503
0.8889	High Similarity	NPC30687
0.8876	High Similarity	NPC59006
0.8864	High Similarity	NPC131466
0.8851	High Similarity	NPC472396
0.8837	High Similarity	NPC290612
0.8804	High Similarity	NPC274200
0.8791	High Similarity	NPC469710
0.8778	High Similarity	NPC211845
0.8778	High Similarity	NPC122083
0.8778	High Similarity	NPC182740
0.8778	High Similarity	NPC256104
0.8736	High Similarity	NPC471240
0.8723	High Similarity	NPC475574
0.8723	High Similarity	NPC476512
0.8723	High Similarity	NPC108227
0.8723	High Similarity	NPC472081
0.8706	High Similarity	NPC296734
0.8696	High Similarity	NPC238796
0.8696	High Similarity	NPC237071
0.8696	High Similarity	NPC203434
0.8696	High Similarity	NPC296936
0.8652	High Similarity	NPC228059
0.8632	High Similarity	NPC114700
0.8632	High Similarity	NPC134967
0.8632	High Similarity	NPC310138
0.8632	High Similarity	NPC470029
0.8617	High Similarity	NPC470030
0.8605	High Similarity	NPC470070
0.8602	High Similarity	NPC470591
0.8587	High Similarity	NPC57964
0.8587	High Similarity	NPC477494
0.8587	High Similarity	NPC94582
0.8587	High Similarity	NPC21897
0.8542	High Similarity	NPC97260
0.8542	High Similarity	NPC139181
0.8542	High Similarity	NPC476837
0.8526	High Similarity	NPC31346
0.8506	High Similarity	NPC474156
0.8495	Intermediate Similarity	NPC156377
0.8488	Intermediate Similarity	NPC475388
0.8478	Intermediate Similarity	NPC191915
0.8478	Intermediate Similarity	NPC151214
0.8471	Intermediate Similarity	NPC7479
0.8471	Intermediate Similarity	NPC248944
0.8471	Intermediate Similarity	NPC257296
0.8462	Intermediate Similarity	NPC473066
0.8454	Intermediate Similarity	NPC475365
0.8421	Intermediate Similarity	NPC41843
0.8404	Intermediate Similarity	NPC210157
0.8391	Intermediate Similarity	NPC241959
0.8353	Intermediate Similarity	NPC477282
0.8353	Intermediate Similarity	NPC81074
0.8333	Intermediate Similarity	NPC11907
0.8333	Intermediate Similarity	NPC133596
0.8333	Intermediate Similarity	NPC476838
0.8333	Intermediate Similarity	NPC64081
0.8333	Intermediate Similarity	NPC477172
0.8333	Intermediate Similarity	NPC476839
0.8333	Intermediate Similarity	NPC474574
0.8315	Intermediate Similarity	NPC155531
0.8315	Intermediate Similarity	NPC215968
0.8315	Intermediate Similarity	NPC477283
0.8298	Intermediate Similarity	NPC252056
0.8298	Intermediate Similarity	NPC472989
0.8298	Intermediate Similarity	NPC145553

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 NPC20822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	4432
0.2-0.3	2973
0.3-0.4	639
0.4-0.5	305
0.5-0.6	239
0.6-0.7	65
0.7-0.8	7
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
0.9205	High Similarity	NPD8171	Discontinued
0.8471	Intermediate Similarity	NPD6928	Phase 2
0.8265	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7991	Discontinued
0.7297	Intermediate Similarity	NPD7516	Approved
0.7232	Intermediate Similarity	NPD8377	Approved
0.7232	Intermediate Similarity	NPD8294	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7168	Intermediate Similarity	NPD8033	Approved
0.7168	Intermediate Similarity	NPD8296	Approved
0.7168	Intermediate Similarity	NPD8335	Approved
0.7168	Intermediate Similarity	NPD8380	Approved
0.7168	Intermediate Similarity	NPD8379	Approved
0.7168	Intermediate Similarity	NPD8378	Approved
0.7011	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8133	Approved
0.6966	Remote Similarity	NPD1810	Approved
0.6966	Remote Similarity	NPD1811	Approved
0.6848	Remote Similarity	NPD6114	Approved
0.6848	Remote Similarity	NPD6697	Approved
0.6848	Remote Similarity	NPD6118	Approved
0.6848	Remote Similarity	NPD6115	Approved
0.6818	Remote Similarity	NPD4787	Phase 1
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7507	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6739	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.663	Remote Similarity	NPD6117	Approved
0.6629	Remote Similarity	NPD2254	Approved
0.6629	Remote Similarity	NPD2686	Approved
0.6629	Remote Similarity	NPD2687	Approved
0.6612	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD8293	Discontinued
0.6581	Remote Similarity	NPD7503	Approved
0.6579	Remote Similarity	NPD6940	Discontinued
0.6545	Remote Similarity	NPD8174	Phase 2
0.6512	Remote Similarity	NPD371	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6496	Remote Similarity	NPD6059	Approved
0.6495	Remote Similarity	NPD3669	Approved
0.6495	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7525	Registered
0.6344	Remote Similarity	NPD3703	Phase 2
0.6333	Remote Similarity	NPD6067	Discontinued
0.632	Remote Similarity	NPD8449	Approved
0.6303	Remote Similarity	NPD6016	Approved
0.6303	Remote Similarity	NPD6015	Approved
0.6296	Remote Similarity	NPD1700	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.627	Remote Similarity	NPD8450	Suspended
0.6264	Remote Similarity	NPD4244	Approved
0.6264	Remote Similarity	NPD4245	Approved
0.625	Remote Similarity	NPD5988	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6179	Remote Similarity	NPD7078	Approved
0.6154	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD3698	Phase 2
0.6154	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8035	Phase 2
0.6126	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7638	Approved
0.6106	Remote Similarity	NPD6686	Approved
0.6078	Remote Similarity	NPD7524	Approved
0.6071	Remote Similarity	NPD2267	Suspended
0.6066	Remote Similarity	NPD8328	Phase 3
0.6055	Remote Similarity	NPD7639	Approved
0.6055	Remote Similarity	NPD7640	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.6034	Remote Similarity	NPD6882	Approved
0.6022	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD6033	Approved
0.598	Remote Similarity	NPD8308	Discontinued
0.5966	Remote Similarity	NPD6009	Approved
0.595	Remote Similarity	NPD6319	Approved
0.5946	Remote Similarity	NPD7632	Discontinued
0.5914	Remote Similarity	NPD4789	Approved
0.5905	Remote Similarity	NPD6700	Approved
0.5905	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5360	Phase 3
0.587	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4159	Approved
0.5849	Remote Similarity	NPD6702	Approved
0.5849	Remote Similarity	NPD6703	Approved
0.5847	Remote Similarity	NPD4632	Approved
0.5839	Remote Similarity	NPD7625	Phase 1
0.5826	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7320	Approved
0.58	Remote Similarity	NPD1779	Approved
0.58	Remote Similarity	NPD1780	Approved
0.5789	Remote Similarity	NPD6402	Approved
0.5789	Remote Similarity	NPD6675	Approved
0.5789	Remote Similarity	NPD5739	Approved
0.5789	Remote Similarity	NPD7128	Approved
0.5784	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6373	Approved
0.5776	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6372	Approved
0.5773	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8418	Phase 2
0.5758	Remote Similarity	NPD7645	Phase 2
0.5714	Remote Similarity	NPD889	Approved
0.5714	Remote Similarity	NPD887	Approved
0.5714	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD894	Approved
0.5714	Remote Similarity	NPD895	Approved
0.57	Remote Similarity	NPD4748	Discontinued
0.569	Remote Similarity	NPD6881	Approved
0.569	Remote Similarity	NPD6899	Approved
0.5686	Remote Similarity	NPD6695	Phase 3
0.5684	Remote Similarity	NPD6081	Approved
0.5678	Remote Similarity	NPD6650	Approved
0.5678	Remote Similarity	NPD6649	Approved
0.5678	Remote Similarity	NPD8130	Phase 1
0.567	Remote Similarity	NPD6942	Approved
0.567	Remote Similarity	NPD7339	Approved
0.5657	Remote Similarity	NPD3671	Phase 1
0.5652	Remote Similarity	NPD6008	Approved
0.5619	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7750	Discontinued
0.5618	Remote Similarity	NPD6123	Approved
0.5603	Remote Similarity	NPD5697	Approved
0.5603	Remote Similarity	NPD5701	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