NPASS Compound

Structure

NPC274417 OpenBabel07101719512D 33 36 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 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 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 28 1 0 0 0 0 13 26 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 29 2 0 0 0 0 16 30 2 0 0 0 0 17 19 1 0 0 0 0 17 31 2 0 0 0 0 18 32 2 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 20 27 1 1 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 26 1 1 0 0 0 23 28 1 0 0 0 0 24 27 1 6 0 0 0 24 33 1 0 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 28 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.29
Volume:	489.387
LogP:	3.32
LogD:	2.743
LogS:	-3.923
# Rotatable Bonds:	5
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.312
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	1.4047274817130528e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.716

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	55.56798553466797%
Volume Distribution (VD):	2.511
Pgp-substrate:	44.85578918457031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	8.21
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.41
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.953
Carcinogencity:	0.217
Eye Corrosion:	0.98
Eye Irritation:	0.296
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC274417

Natural Product ID:	NPC274417
*Common Name:**	12Alpha-Acetoxy-24-Methyl-24-Oxoscalar-16-En-22,25-Dial
IUPAC Name:	[(4aR,4bS,6S,6aS,7R,10aS,10bS,12aS)-8-acetyl-4a,7-diformyl-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate
Synonyms:
Standard InCHIKey:	YRTZXBPLXPUTPV-GPWSRLOJSA-N
Standard InCHI:	InChI=1S/C28H40O5/c1-17(31)19-8-9-22-26(5)13-10-21-25(3,4)11-7-12-28(21,16-30)23(26)14-24(33-18(2)32)27(22,6)20(19)15-29/h8,15-16,20-24H,7,9-14H2,1-6H3/t20-,21-,22-,23-,24-,26-,27+,28+/m0/s1
SMILES:	O=C[C@H]1C(=CC[C@@H]2[C@]1(C)[C@@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C=O)CCCC2(C)C)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510804
PubChem CID:	23425818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33170	lendenfeldia chondrodes	Species	Thorectidae	Eukaryota	n.a.	palauan	n.a.	PMID[9917306]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	3

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3973	Individual Protein	Endothelial PAS domain-containing protein 1	Homo sapiens	EC50	=	4200.0	nM	PMID[524770]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	10.0	%	PMID[524769]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	55.0	%	PMID[524769]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	75.0	%	PMID[524769]

☑ 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 NPC274417 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	247
0.1-0.2	1603
0.2-0.3	5432
0.3-0.4	11288
0.4-0.5	11008
0.5-0.6	6550
0.6-0.7	4753
0.7-0.8	1659
0.8-0.85	127
0.85-0.9	20
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC269729
0.9565	High Similarity	NPC475202
0.9565	High Similarity	NPC475385
0.9565	High Similarity	NPC475392
0.9545	High Similarity	NPC328141
0.9263	High Similarity	NPC282233
0.9263	High Similarity	NPC95585
0.9	High Similarity	NPC469546
0.8913	High Similarity	NPC474185
0.8842	High Similarity	NPC471966
0.883	High Similarity	NPC469545
0.883	High Similarity	NPC5532
0.883	High Similarity	NPC61369
0.8764	High Similarity	NPC2709
0.8737	High Similarity	NPC473456
0.8737	High Similarity	NPC226986
0.871	High Similarity	NPC79117
0.8696	High Similarity	NPC159748
0.8696	High Similarity	NPC101651
0.8681	High Similarity	NPC224145
0.8636	High Similarity	NPC470813
0.8632	High Similarity	NPC471039
0.8617	High Similarity	NPC471040
0.8617	High Similarity	NPC74751
0.8602	High Similarity	NPC230064
0.8571	High Similarity	NPC162107
0.8571	High Similarity	NPC30421
0.8571	High Similarity	NPC46912
0.8542	High Similarity	NPC292133
0.8542	High Similarity	NPC23680
0.8526	High Similarity	NPC139570
0.8511	High Similarity	NPC295643
0.8511	High Similarity	NPC272075
0.8511	High Similarity	NPC214756
0.8511	High Similarity	NPC151722
0.8485	Intermediate Similarity	NPC254202
0.8478	Intermediate Similarity	NPC474925
0.8478	Intermediate Similarity	NPC474845
0.8462	Intermediate Similarity	NPC471042
0.8462	Intermediate Similarity	NPC91525
0.8462	Intermediate Similarity	NPC9892
0.8462	Intermediate Similarity	NPC329943
0.8462	Intermediate Similarity	NPC10005
0.8454	Intermediate Similarity	NPC478056
0.8409	Intermediate Similarity	NPC474956
0.8404	Intermediate Similarity	NPC233455
0.8404	Intermediate Similarity	NPC145067
0.8404	Intermediate Similarity	NPC65120
0.8404	Intermediate Similarity	NPC4036
0.8404	Intermediate Similarity	NPC218301
0.8404	Intermediate Similarity	NPC158030
0.84	Intermediate Similarity	NPC189616
0.8387	Intermediate Similarity	NPC475049
0.8387	Intermediate Similarity	NPC477973
0.8367	Intermediate Similarity	NPC104861
0.8351	Intermediate Similarity	NPC26413
0.8351	Intermediate Similarity	NPC89225
0.8333	Intermediate Similarity	NPC139459
0.83	Intermediate Similarity	NPC179208
0.83	Intermediate Similarity	NPC36321
0.83	Intermediate Similarity	NPC478057
0.8298	Intermediate Similarity	NPC291028
0.8298	Intermediate Similarity	NPC152467
0.8298	Intermediate Similarity	NPC113989
0.8298	Intermediate Similarity	NPC120840
0.8298	Intermediate Similarity	NPC474842
0.8298	Intermediate Similarity	NPC474728
0.8298	Intermediate Similarity	NPC475965
0.8283	Intermediate Similarity	NPC310981
0.828	Intermediate Similarity	NPC206060
0.828	Intermediate Similarity	NPC473229
0.8265	Intermediate Similarity	NPC194196
0.8265	Intermediate Similarity	NPC176845
0.8247	Intermediate Similarity	NPC122324
0.8247	Intermediate Similarity	NPC106425
0.8247	Intermediate Similarity	NPC151725
0.8247	Intermediate Similarity	NPC111684
0.8247	Intermediate Similarity	NPC58052
0.8247	Intermediate Similarity	NPC167193
0.8247	Intermediate Similarity	NPC472806
0.8247	Intermediate Similarity	NPC98874
0.8229	Intermediate Similarity	NPC159410
0.8229	Intermediate Similarity	NPC470697
0.8229	Intermediate Similarity	NPC474529
0.8229	Intermediate Similarity	NPC169751
0.8229	Intermediate Similarity	NPC272635
0.8222	Intermediate Similarity	NPC163236
0.8218	Intermediate Similarity	NPC470297
0.8211	Intermediate Similarity	NPC470590
0.8211	Intermediate Similarity	NPC77099
0.8211	Intermediate Similarity	NPC105189
0.8211	Intermediate Similarity	NPC60755
0.8211	Intermediate Similarity	NPC285184
0.82	Intermediate Similarity	NPC136289
0.8191	Intermediate Similarity	NPC184663
0.8191	Intermediate Similarity	NPC30522
0.8191	Intermediate Similarity	NPC50070
0.8163	Intermediate Similarity	NPC476768
0.8163	Intermediate Similarity	NPC38530
0.8163	Intermediate Similarity	NPC170131
0.8163	Intermediate Similarity	NPC84335
0.8155	Intermediate Similarity	NPC189075
0.8155	Intermediate Similarity	NPC275539
0.8144	Intermediate Similarity	NPC148523
0.8125	Intermediate Similarity	NPC49776
0.8125	Intermediate Similarity	NPC294263
0.8125	Intermediate Similarity	NPC474436
0.8125	Intermediate Similarity	NPC86368
0.8125	Intermediate Similarity	NPC298554
0.8125	Intermediate Similarity	NPC476416
0.8125	Intermediate Similarity	NPC107674
0.8125	Intermediate Similarity	NPC141497
0.8125	Intermediate Similarity	NPC63118
0.8125	Intermediate Similarity	NPC170220
0.8119	Intermediate Similarity	NPC264048
0.8119	Intermediate Similarity	NPC95899
0.8119	Intermediate Similarity	NPC275583
0.8111	Intermediate Similarity	NPC475665
0.8105	Intermediate Similarity	NPC273621
0.8105	Intermediate Similarity	NPC227467
0.8105	Intermediate Similarity	NPC290614
0.8105	Intermediate Similarity	NPC210037
0.8105	Intermediate Similarity	NPC477872
0.8105	Intermediate Similarity	NPC7260
0.8105	Intermediate Similarity	NPC120968
0.8105	Intermediate Similarity	NPC193750
0.8105	Intermediate Similarity	NPC18872
0.81	Intermediate Similarity	NPC81530
0.8085	Intermediate Similarity	NPC472802
0.8085	Intermediate Similarity	NPC80335
0.8085	Intermediate Similarity	NPC40552
0.8085	Intermediate Similarity	NPC246708
0.8085	Intermediate Similarity	NPC182797
0.8085	Intermediate Similarity	NPC52169
0.8081	Intermediate Similarity	NPC260149
0.8081	Intermediate Similarity	NPC58942
0.8081	Intermediate Similarity	NPC188833
0.8077	Intermediate Similarity	NPC310546
0.8077	Intermediate Similarity	NPC112457
0.8068	Intermediate Similarity	NPC472300
0.8065	Intermediate Similarity	NPC195640
0.8065	Intermediate Similarity	NPC325594
0.8065	Intermediate Similarity	NPC73038
0.8065	Intermediate Similarity	NPC220478
0.8061	Intermediate Similarity	NPC327179
0.8061	Intermediate Similarity	NPC471775
0.8061	Intermediate Similarity	NPC192428
0.8061	Intermediate Similarity	NPC219353
0.8058	Intermediate Similarity	NPC220974
0.8058	Intermediate Similarity	NPC110496
0.8043	Intermediate Similarity	NPC470812
0.8043	Intermediate Similarity	NPC312660
0.8041	Intermediate Similarity	NPC476415
0.8041	Intermediate Similarity	NPC78580
0.8041	Intermediate Similarity	NPC471207
0.8041	Intermediate Similarity	NPC222047
0.8041	Intermediate Similarity	NPC23621
0.8041	Intermediate Similarity	NPC184006
0.8041	Intermediate Similarity	NPC209868
0.8041	Intermediate Similarity	NPC294266
0.8041	Intermediate Similarity	NPC296164
0.8022	Intermediate Similarity	NPC286786
0.8022	Intermediate Similarity	NPC142683
0.8021	Intermediate Similarity	NPC470230
0.8021	Intermediate Similarity	NPC187722
0.8021	Intermediate Similarity	NPC212301
0.8021	Intermediate Similarity	NPC297265
0.8021	Intermediate Similarity	NPC474525
0.8021	Intermediate Similarity	NPC86266
0.8021	Intermediate Similarity	NPC38754
0.8021	Intermediate Similarity	NPC110657
0.802	Intermediate Similarity	NPC40918
0.8	Intermediate Similarity	NPC225585
0.8	Intermediate Similarity	NPC267517
0.8	Intermediate Similarity	NPC274330
0.8	Intermediate Similarity	NPC290972
0.8	Intermediate Similarity	NPC263393
0.8	Intermediate Similarity	NPC143232
0.8	Intermediate Similarity	NPC64872
0.8	Intermediate Similarity	NPC127689
0.8	Intermediate Similarity	NPC470588
0.8	Intermediate Similarity	NPC476274
0.8	Intermediate Similarity	NPC293048
0.8	Intermediate Similarity	NPC35751
0.8	Intermediate Similarity	NPC61543
0.8	Intermediate Similarity	NPC121798
0.8	Intermediate Similarity	NPC59263
0.8	Intermediate Similarity	NPC270768
0.8	Intermediate Similarity	NPC234346
0.8	Intermediate Similarity	NPC198664
0.8	Intermediate Similarity	NPC25906
0.8	Intermediate Similarity	NPC117685
0.8	Intermediate Similarity	NPC470906
0.8	Intermediate Similarity	NPC73995
0.8	Intermediate Similarity	NPC130520
0.8	Intermediate Similarity	NPC471041
0.7981	Intermediate Similarity	NPC89171
0.7981	Intermediate Similarity	NPC476802
0.798	Intermediate Similarity	NPC187933
0.798	Intermediate Similarity	NPC10057

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 NPC274417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1862
0.2-0.3	3917
0.3-0.4	2059
0.4-0.5	681
0.5-0.6	186
0.6-0.7	139
0.7-0.8	77
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9022	High Similarity	NPD7900	Approved
0.9022	High Similarity	NPD7901	Clinical (unspecified phase)
0.8737	High Similarity	NPD7902	Approved
0.8617	High Similarity	NPD7748	Approved
0.8571	High Similarity	NPD3573	Approved
0.8404	Intermediate Similarity	NPD7515	Phase 2
0.828	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6409	Approved
0.8065	Intermediate Similarity	NPD7334	Approved
0.8065	Intermediate Similarity	NPD6684	Approved
0.8065	Intermediate Similarity	NPD7146	Approved
0.8065	Intermediate Similarity	NPD5330	Approved
0.8065	Intermediate Similarity	NPD7521	Approved
0.8061	Intermediate Similarity	NPD4697	Phase 3
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.7925	Intermediate Similarity	NPD6650	Approved
0.7925	Intermediate Similarity	NPD6649	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.7905	Intermediate Similarity	NPD6373	Approved
0.7895	Intermediate Similarity	NPD5737	Approved
0.7895	Intermediate Similarity	NPD6672	Approved
0.7895	Intermediate Similarity	NPD6903	Approved
0.7835	Intermediate Similarity	NPD6079	Approved
0.7812	Intermediate Similarity	NPD5328	Approved
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD6008	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5697	Approved
0.7684	Intermediate Similarity	NPD3618	Phase 1
0.7664	Intermediate Similarity	NPD7290	Approved
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.7653	Intermediate Similarity	NPD8034	Phase 2
0.7653	Intermediate Similarity	NPD8035	Phase 2
0.7642	Intermediate Similarity	NPD6011	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD6869	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7579	Intermediate Similarity	NPD1694	Approved
0.757	Intermediate Similarity	NPD6014	Approved
0.757	Intermediate Similarity	NPD6012	Approved
0.757	Intermediate Similarity	NPD6013	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7525	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7732	Phase 3
0.7525	Intermediate Similarity	NPD5221	Approved
0.7525	Intermediate Similarity	NPD5222	Approved
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.7451	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD6904	Approved
0.7449	Intermediate Similarity	NPD6080	Approved
0.7449	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7638	Approved
0.7327	Intermediate Similarity	NPD6001	Approved
0.7321	Intermediate Similarity	NPD6868	Approved
0.7308	Intermediate Similarity	NPD4696	Approved
0.7308	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD5286	Approved
0.7308	Intermediate Similarity	NPD5285	Approved
0.7308	Intermediate Similarity	NPD7640	Approved
0.7282	Intermediate Similarity	NPD4755	Approved
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7115	Discovery
0.7238	Intermediate Similarity	NPD5223	Approved
0.7216	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5696	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7184	Intermediate Similarity	NPD7614	Phase 1
0.7179	Intermediate Similarity	NPD8328	Phase 3
0.7172	Intermediate Similarity	NPD5208	Approved
0.717	Intermediate Similarity	NPD5225	Approved
0.717	Intermediate Similarity	NPD4633	Approved
0.717	Intermediate Similarity	NPD5226	Approved
0.717	Intermediate Similarity	NPD5211	Phase 2
0.717	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.7143	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7100	Approved
0.713	Intermediate Similarity	NPD7101	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7129	Intermediate Similarity	NPD6050	Approved
0.7129	Intermediate Similarity	NPD6411	Approved
0.7113	Intermediate Similarity	NPD3668	Phase 3
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3666	Approved
0.7113	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.7103	Intermediate Similarity	NPD5174	Approved
0.7103	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD5695	Phase 3
0.7083	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD4202	Approved
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.7037	Intermediate Similarity	NPD5141	Approved
0.703	Intermediate Similarity	NPD5692	Phase 3
0.703	Intermediate Similarity	NPD5207	Approved
0.7009	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5694	Approved
0.6957	Remote Similarity	NPD6009	Approved
0.6947	Remote Similarity	NPD7645	Phase 2
0.6944	Remote Similarity	NPD4754	Approved
0.6942	Remote Similarity	NPD7736	Approved
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6101	Approved
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6319	Approved
0.6917	Remote Similarity	NPD7507	Approved
0.6909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7604	Phase 2
0.6887	Remote Similarity	NPD4225	Approved
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD5983	Phase 2
0.6864	Remote Similarity	NPD6908	Approved
0.6847	Remote Similarity	NPD5128	Approved
0.6847	Remote Similarity	NPD4730	Approved
0.6847	Remote Similarity	NPD4729	Approved
0.6847	Remote Similarity	NPD5168	Approved
0.6833	Remote Similarity	NPD7492	Approved
0.6818	Remote Similarity	NPD4768	Approved
0.6818	Remote Similarity	NPD4767	Approved
0.6813	Remote Similarity	NPD4691	Approved
0.6796	Remote Similarity	NPD5281	Approved
0.6796	Remote Similarity	NPD5284	Approved
0.6789	Remote Similarity	NPD6052	Approved
0.678	Remote Similarity	NPD6054	Approved
0.6777	Remote Similarity	NPD6336	Discontinued
0.6777	Remote Similarity	NPD6616	Approved
0.6765	Remote Similarity	NPD4753	Phase 2
0.6762	Remote Similarity	NPD5210	Approved
0.6762	Remote Similarity	NPD4629	Approved
0.6757	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD6614	Approved
0.6748	Remote Similarity	NPD7319	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6735	Remote Similarity	NPD4221	Approved
0.6726	Remote Similarity	NPD5249	Phase 3
0.6726	Remote Similarity	NPD5135	Approved
0.6726	Remote Similarity	NPD5250	Approved
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5247	Approved
0.6726	Remote Similarity	NPD5169	Approved
0.6726	Remote Similarity	NPD5248	Approved
0.6726	Remote Similarity	NPD4634	Approved
0.6726	Remote Similarity	NPD5251	Approved
0.6726	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7078	Approved
0.6703	Remote Similarity	NPD4137	Phase 3
0.67	Remote Similarity	NPD5329	Approved
0.6697	Remote Similarity	NPD7632	Discontinued
0.6696	Remote Similarity	NPD7094	Approved
0.6696	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD6059	Approved
0.6634	Remote Similarity	NPD5279	Phase 3
0.663	Remote Similarity	NPD4747	Approved
0.6604	Remote Similarity	NPD5654	Approved
0.6602	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD4197	Approved
0.6596	Remote Similarity	NPD4058	Approved
0.6585	Remote Similarity	NPD8293	Discontinued
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6571	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD5779	Approved
0.6559	Remote Similarity	NPD5777	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6686	Approved
0.6531	Remote Similarity	NPD7525	Registered
0.6529	Remote Similarity	NPD5988	Approved
0.65	Remote Similarity	NPD4788	Approved
0.6496	Remote Similarity	NPD5167	Approved
0.6495	Remote Similarity	NPD3617	Approved
0.6491	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5959	Approved
0.6471	Remote Similarity	NPD4138	Approved
0.6471	Remote Similarity	NPD4688	Approved
0.6471	Remote Similarity	NPD4623	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