NPASS Compound

Structure

NPC6605 OpenBabel07101718192D 33 36 0 0 1 0 0 0 0 0999 V2000 -5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6786 -5.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0313 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7004 -5.0780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3403 -6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 6 0 0 0 16 18 1 0 0 0 0 17 2 1 6 0 0 0 17 20 1 0 0 0 0 18 3 1 1 0 0 0 19 30 1 1 0 0 0 20 27 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 32 1 6 0 0 0 24 26 1 1 0 0 0 24 28 1 0 0 0 0 25 27 1 1 0 0 0 25 28 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.35
Volume:	499.933
LogP:	3.741
LogD:	3.626
LogS:	-4.004
# Rotatable Bonds:	5
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	5.255
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.11
MDCK Permeability:	7.326898048631847e-05
Pgp-inhibitor:	0.35
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.626
20% Bioavailability (F20%):	0.237
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	84.43224334716797%
Volume Distribution (VD):	0.734
Pgp-substrate:	1.6934762001037598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	1.874
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.481
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.653
Carcinogencity:	0.044
Eye Corrosion:	0.006
Eye Irritation:	0.044
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC6605

Natural Product ID:	NPC6605
*Common Name:**	Certonardosterol C2
IUPAC Name:	(3S,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-[(E,2R,5R,6S)-7-hydroxy-5,6-dimethylhept-3-en-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-tetrol
Synonyms:	Certonardosterol C2
Standard InCHIKey:	CAJSDLMSCZXCNV-WIGUABAWSA-N
Standard InCHI:	InChI=1S/C28H48O5/c1-16(18(3)15-29)6-7-17(2)20-13-22(31)25-27(20,5)11-9-24-26(4)10-8-19(30)12-21(26)23(32)14-28(24,25)33/h6-7,16-25,29-33H,8-15H2,1-5H3/b7-6+/t16-,17-,18-,19+,20-,21-,22-,23+,24-,25-,26+,27-,28+/m1/s1
SMILES:	OC[C@H]([C@@H](/C=C/[C@H]([C@H]1C[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)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465356
PubChem CID:	11408669
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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	=	0.15	ug ml-1	PMID[475018]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.16	ug ml-1	PMID[475018]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	<	0.1	ug ml-1	PMID[475018]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.08	ug ml-1	PMID[475018]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	0.25	ug ml-1	PMID[475018]

☑ 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 NPC6605 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	186
0.1-0.2	1563
0.2-0.3	6346
0.3-0.4	15557
0.4-0.5	7657
0.5-0.6	4897
0.6-0.7	4754
0.7-0.8	1478
0.8-0.85	181
0.85-0.9	58
0.9-0.95	11
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC201273
0.9639	High Similarity	NPC109744
0.9625	High Similarity	NPC193870
0.9625	High Similarity	NPC141941
0.9524	High Similarity	NPC475751
0.9524	High Similarity	NPC473956
0.9506	High Similarity	NPC127606
0.9506	High Similarity	NPC475798
0.9398	High Similarity	NPC474657
0.9398	High Similarity	NPC186145
0.9383	High Similarity	NPC110778
0.9383	High Similarity	NPC477818
0.9286	High Similarity	NPC475664
0.9277	High Similarity	NPC139724
0.9146	High Similarity	NPC232023
0.9048	High Similarity	NPC299068
0.9048	High Similarity	NPC24277
0.9036	High Similarity	NPC124172
0.9012	High Similarity	NPC236237
0.9012	High Similarity	NPC322313
0.9012	High Similarity	NPC102253
0.8929	High Similarity	NPC470360
0.8916	High Similarity	NPC113978
0.8889	High Similarity	NPC80530
0.8889	High Similarity	NPC273410
0.8889	High Similarity	NPC477226
0.8837	High Similarity	NPC212596
0.8837	High Similarity	NPC475605
0.8837	High Similarity	NPC4574
0.8824	High Similarity	NPC121981
0.881	High Similarity	NPC209802
0.8795	High Similarity	NPC1272
0.8795	High Similarity	NPC470614
0.878	High Similarity	NPC71535
0.878	High Similarity	NPC78545
0.8765	High Similarity	NPC244385
0.8765	High Similarity	NPC138621
0.8765	High Similarity	NPC6978
0.8765	High Similarity	NPC31828
0.8765	High Similarity	NPC167037
0.8765	High Similarity	NPC285761
0.8765	High Similarity	NPC477817
0.8765	High Similarity	NPC477819
0.875	High Similarity	NPC41554
0.875	High Similarity	NPC97404
0.875	High Similarity	NPC275671
0.8736	High Similarity	NPC101886
0.8736	High Similarity	NPC105495
0.8721	High Similarity	NPC304083
0.8706	High Similarity	NPC318390
0.869	High Similarity	NPC207013
0.869	High Similarity	NPC216420
0.869	High Similarity	NPC85095
0.869	High Similarity	NPC211135
0.8675	High Similarity	NPC470383
0.8659	High Similarity	NPC1319
0.8636	High Similarity	NPC291484
0.8636	High Similarity	NPC80561
0.8636	High Similarity	NPC11216
0.8636	High Similarity	NPC204188
0.8636	High Similarity	NPC329596
0.8636	High Similarity	NPC3345
0.8625	High Similarity	NPC103822
0.8621	High Similarity	NPC470542
0.8605	High Similarity	NPC269058
0.8605	High Similarity	NPC6391
0.8605	High Similarity	NPC261266
0.8605	High Similarity	NPC293287
0.8605	High Similarity	NPC152808
0.8605	High Similarity	NPC71520
0.8588	High Similarity	NPC474493
0.8588	High Similarity	NPC256567
0.8588	High Similarity	NPC255882
0.8571	High Similarity	NPC30166
0.8571	High Similarity	NPC471903
0.8571	High Similarity	NPC296701
0.8571	High Similarity	NPC218616
0.8554	High Similarity	NPC475679
0.8554	High Similarity	NPC26117
0.8554	High Similarity	NPC13554
0.8537	High Similarity	NPC148977
0.8523	High Similarity	NPC470361
0.8523	High Similarity	NPC74258
0.8523	High Similarity	NPC138974
0.8519	High Similarity	NPC237460
0.85	High Similarity	NPC304499
0.8478	Intermediate Similarity	NPC474994
0.8478	Intermediate Similarity	NPC316604
0.8478	Intermediate Similarity	NPC476021
0.8478	Intermediate Similarity	NPC476040
0.8471	Intermediate Similarity	NPC134481
0.8471	Intermediate Similarity	NPC470558
0.8471	Intermediate Similarity	NPC82623
0.8471	Intermediate Similarity	NPC470929
0.8444	Intermediate Similarity	NPC98193
0.8434	Intermediate Similarity	NPC475727
0.8434	Intermediate Similarity	NPC24504
0.8434	Intermediate Similarity	NPC472742
0.8434	Intermediate Similarity	NPC476316
0.8434	Intermediate Similarity	NPC80297
0.8434	Intermediate Similarity	NPC472463
0.8434	Intermediate Similarity	NPC116119
0.8427	Intermediate Similarity	NPC470390
0.8427	Intermediate Similarity	NPC270511
0.8427	Intermediate Similarity	NPC245410
0.8427	Intermediate Similarity	NPC14380
0.8427	Intermediate Similarity	NPC192437
0.8409	Intermediate Similarity	NPC2158
0.8409	Intermediate Similarity	NPC133588
0.8395	Intermediate Similarity	NPC3403
0.8372	Intermediate Similarity	NPC86238
0.8372	Intermediate Similarity	NPC205845
0.837	Intermediate Similarity	NPC288970
0.8353	Intermediate Similarity	NPC248886
0.8352	Intermediate Similarity	NPC65402
0.8352	Intermediate Similarity	NPC127718
0.8333	Intermediate Similarity	NPC47149
0.8333	Intermediate Similarity	NPC210268
0.8313	Intermediate Similarity	NPC85346
0.8313	Intermediate Similarity	NPC301707
0.8313	Intermediate Similarity	NPC302041
0.8313	Intermediate Similarity	NPC65897
0.8313	Intermediate Similarity	NPC472499
0.8313	Intermediate Similarity	NPC475
0.8313	Intermediate Similarity	NPC472502
0.8313	Intermediate Similarity	NPC472500
0.8313	Intermediate Similarity	NPC472501
0.8313	Intermediate Similarity	NPC42853
0.8313	Intermediate Similarity	NPC477522
0.8313	Intermediate Similarity	NPC87604
0.8295	Intermediate Similarity	NPC271967
0.8295	Intermediate Similarity	NPC475313
0.8293	Intermediate Similarity	NPC189883
0.8293	Intermediate Similarity	NPC129165
0.8293	Intermediate Similarity	NPC63958
0.8293	Intermediate Similarity	NPC134330
0.8276	Intermediate Similarity	NPC474189
0.8276	Intermediate Similarity	NPC474349
0.8272	Intermediate Similarity	NPC308440
0.8272	Intermediate Similarity	NPC472503
0.8261	Intermediate Similarity	NPC8774
0.8242	Intermediate Similarity	NPC310013
0.8242	Intermediate Similarity	NPC27531
0.8235	Intermediate Similarity	NPC157655
0.8235	Intermediate Similarity	NPC249423
0.8235	Intermediate Similarity	NPC242350
0.8222	Intermediate Similarity	NPC295668
0.8214	Intermediate Similarity	NPC49599
0.8214	Intermediate Similarity	NPC49627
0.8211	Intermediate Similarity	NPC474022
0.8202	Intermediate Similarity	NPC474668
0.8202	Intermediate Similarity	NPC193360
0.8202	Intermediate Similarity	NPC67872
0.8193	Intermediate Similarity	NPC138502
0.8193	Intermediate Similarity	NPC128951
0.8193	Intermediate Similarity	NPC260301
0.8193	Intermediate Similarity	NPC198968
0.8193	Intermediate Similarity	NPC185915
0.8193	Intermediate Similarity	NPC192046
0.8193	Intermediate Similarity	NPC318495
0.8193	Intermediate Similarity	NPC202540
0.8193	Intermediate Similarity	NPC307336
0.8193	Intermediate Similarity	NPC477227
0.8193	Intermediate Similarity	NPC471798
0.8193	Intermediate Similarity	NPC105208
0.8193	Intermediate Similarity	NPC155986
0.8193	Intermediate Similarity	NPC302578
0.8193	Intermediate Similarity	NPC214570
0.8191	Intermediate Similarity	NPC191565
0.8182	Intermediate Similarity	NPC94462
0.8172	Intermediate Similarity	NPC304899
0.8172	Intermediate Similarity	NPC227583
0.8172	Intermediate Similarity	NPC98457
0.8172	Intermediate Similarity	NPC12103
0.8172	Intermediate Similarity	NPC253115
0.8171	Intermediate Similarity	NPC471723
0.8171	Intermediate Similarity	NPC257347
0.8171	Intermediate Similarity	NPC317242
0.8171	Intermediate Similarity	NPC141071
0.8161	Intermediate Similarity	NPC470077
0.8161	Intermediate Similarity	NPC469878
0.8161	Intermediate Similarity	NPC478102
0.8152	Intermediate Similarity	NPC144202
0.8152	Intermediate Similarity	NPC111015
0.8152	Intermediate Similarity	NPC209662
0.814	Intermediate Similarity	NPC20853
0.814	Intermediate Similarity	NPC201852
0.814	Intermediate Similarity	NPC87489
0.814	Intermediate Similarity	NPC101462
0.814	Intermediate Similarity	NPC49964
0.814	Intermediate Similarity	NPC50964
0.8125	Intermediate Similarity	NPC251201
0.8125	Intermediate Similarity	NPC232925
0.8125	Intermediate Similarity	NPC63588
0.8118	Intermediate Similarity	NPC164840
0.8118	Intermediate Similarity	NPC241290
0.8118	Intermediate Similarity	NPC236112
0.8118	Intermediate Similarity	NPC209944
0.8095	Intermediate Similarity	NPC312328
0.8095	Intermediate Similarity	NPC18857

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 NPC6605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1792
0.2-0.3	4474
0.3-0.4	1912
0.4-0.5	369
0.5-0.6	161
0.6-0.7	147
0.7-0.8	123
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9012	High Similarity	NPD7525	Registered
0.8072	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6932	Approved
0.7955	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6942	Approved
0.7952	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD6930	Phase 2
0.7907	Intermediate Similarity	NPD6931	Approved
0.7889	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6695	Phase 3
0.7831	Intermediate Similarity	NPD4784	Approved
0.7831	Intermediate Similarity	NPD4785	Approved
0.7805	Intermediate Similarity	NPD4243	Approved
0.7791	Intermediate Similarity	NPD7645	Phase 2
0.7791	Intermediate Similarity	NPD6929	Approved
0.7732	Intermediate Similarity	NPD4696	Approved
0.7732	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5286	Approved
0.7708	Intermediate Similarity	NPD4755	Approved
0.7701	Intermediate Similarity	NPD7514	Phase 3
0.7674	Intermediate Similarity	NPD7145	Approved
0.766	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD6924	Approved
0.7619	Intermediate Similarity	NPD6926	Approved
0.7586	Intermediate Similarity	NPD6683	Phase 2
0.7576	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD5226	Approved
0.7576	Intermediate Similarity	NPD4633	Approved
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7576	Intermediate Similarity	NPD5224	Approved
0.7561	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5776	Phase 2
0.7558	Intermediate Similarity	NPD6925	Approved
0.7551	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7332	Phase 2
0.75	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD7524	Approved
0.7475	Intermediate Similarity	NPD5223	Approved
0.7473	Intermediate Similarity	NPD6893	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7442	Intermediate Similarity	NPD6933	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7416	Intermediate Similarity	NPD6902	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7386	Intermediate Similarity	NPD4195	Approved
0.7381	Intermediate Similarity	NPD7151	Approved
0.7381	Intermediate Similarity	NPD7150	Approved
0.7381	Intermediate Similarity	NPD7152	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7379	Intermediate Similarity	NPD6881	Approved
0.7374	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD6079	Approved
0.7363	Intermediate Similarity	NPD4786	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7326	Intermediate Similarity	NPD5275	Approved
0.7326	Intermediate Similarity	NPD4190	Phase 3
0.7303	Intermediate Similarity	NPD7509	Discontinued
0.7282	Intermediate Similarity	NPD5697	Approved
0.7262	Intermediate Similarity	NPD4787	Phase 1
0.7262	Intermediate Similarity	NPD7144	Approved
0.7262	Intermediate Similarity	NPD7143	Approved
0.7248	Intermediate Similarity	NPD7328	Approved
0.7248	Intermediate Similarity	NPD7327	Approved
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7222	Intermediate Similarity	NPD6898	Phase 1
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD4730	Approved
0.7212	Intermediate Similarity	NPD4729	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.7188	Intermediate Similarity	NPD7087	Discontinued
0.7184	Intermediate Similarity	NPD4767	Approved
0.7184	Intermediate Similarity	NPD4768	Approved
0.7182	Intermediate Similarity	NPD7516	Approved
0.7174	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD3133	Approved
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6922	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7103	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5251	Approved
0.7075	Intermediate Similarity	NPD5250	Approved
0.7075	Intermediate Similarity	NPD5248	Approved
0.7075	Intermediate Similarity	NPD5249	Phase 3
0.7075	Intermediate Similarity	NPD5247	Approved
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD4788	Approved
0.7054	Intermediate Similarity	NPD8379	Approved
0.7054	Intermediate Similarity	NPD8378	Approved
0.7054	Intermediate Similarity	NPD8380	Approved
0.7054	Intermediate Similarity	NPD8335	Approved
0.7054	Intermediate Similarity	NPD8296	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7048	Intermediate Similarity	NPD5128	Approved
0.7037	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD6054	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6957	Remote Similarity	NPD4221	Approved
0.6939	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6928	Phase 2
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5329	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.69	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD6115	Approved
0.6889	Remote Similarity	NPD6114	Approved
0.6889	Remote Similarity	NPD6697	Approved
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5127	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6009	Approved
0.6842	Remote Similarity	NPD6370	Approved
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD7515	Phase 2
0.6814	Remote Similarity	NPD6059	Approved
0.6814	Remote Similarity	NPD6319	Approved
0.6809	Remote Similarity	NPD4197	Approved
0.6804	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6778	Remote Similarity	NPD6116	Phase 1
0.6754	Remote Similarity	NPD6016	Approved
0.6754	Remote Similarity	NPD6015	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6735	Remote Similarity	NPD7136	Phase 2
0.6731	Remote Similarity	NPD7632	Discontinued
0.6726	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6724	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD5988	Approved
0.6695	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD7319	Approved
0.6638	Remote Similarity	NPD7604	Phase 2
0.6637	Remote Similarity	NPD6335	Approved
0.6635	Remote Similarity	NPD4159	Approved
0.6634	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD3668	Phase 3
0.661	Remote Similarity	NPD7078	Approved
0.6609	Remote Similarity	NPD5983	Phase 2
0.6607	Remote Similarity	NPD6274	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.6602	Remote Similarity	NPD5696	Approved
0.6591	Remote Similarity	NPD4809	Clinical (unspecified phase)

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