NPASS Compound

Structure

NPC5532 OpenBabel07101719522D 30 33 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 -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 -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 2 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 27 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 29 2 0 0 0 0 17 18 1 0 0 0 0 18 25 1 6 0 0 0 19 23 1 0 0 0 0 19 26 1 1 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 22 25 1 6 0 0 0 22 30 1 0 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 26 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.29
Volume:	451.278
LogP:	2.73
LogD:	3.067
LogS:	-3.83
# Rotatable Bonds:	3
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	5.057
Fsp3:	0.846
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:	-4.704
MDCK Permeability:	1.84241944225505e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.908
Plasma Protein Binding (PPB):	56.193824768066406%
Volume Distribution (VD):	1.852
Pgp-substrate:	41.79011154174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	8.889
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.752
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.954
Carcinogencity:	0.37
Eye Corrosion:	0.232
Eye Irritation:	0.182
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC5532

Natural Product ID:	NPC5532
*Common Name:**	Rel-12Alpha,22-Dihydroxy-24-Methyl-24-Oxoscalar-16-En-18-Alpha-25-Al
IUPAC Name:	(1S,4aS,4bR,6aS,10aR,10bS,12S,12aS)-2-acetyl-12-hydroxy-10a-(hydroxymethyl)-4b,7,7,12a-tetramethyl-1,4,4a,5,6,6a,8,9,10,10b,11,12-dodecahydrochrysene-1-carbaldehyde
Synonyms:
Standard InCHIKey:	OGLFTTHUASEWEH-LNJOPRJUSA-N
Standard InCHI:	InChI=1S/C26H40O4/c1-16(29)17-7-8-20-24(4)12-9-19-23(2,3)10-6-11-26(19,15-28)21(24)13-22(30)25(20,5)18(17)14-27/h7,14,18-22,28,30H,6,8-13,15H2,1-5H3/t18-,19+,20+,21+,22+,24+,25-,26-/m1/s1
SMILES:	O=C[C@@H]1C(=CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(CO)CCCC2(C)C)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387628
PubChem CID:	71658745
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
NPO32746	madagascan sponges	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23623678]

☑ 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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	1830.0	nM	PMID[565997]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	260.0	nM	PMID[565997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[565997]

☑ 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 NPC5532 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	217
0.1-0.2	1439
0.2-0.3	5040
0.3-0.4	10626
0.4-0.5	11911
0.5-0.6	6491
0.6-0.7	4869
0.7-0.8	1909
0.8-0.85	164
0.85-0.9	23
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC61369
1.0	High Similarity	NPC469545
0.9368	High Similarity	NPC95585
0.9368	High Similarity	NPC282233
0.9213	High Similarity	NPC474925
0.913	High Similarity	NPC471207
0.9	High Similarity	NPC206060
0.8901	High Similarity	NPC184663
0.883	High Similarity	NPC274417
0.8791	High Similarity	NPC472802
0.8764	High Similarity	NPC470812
0.8737	High Similarity	NPC192428
0.8723	High Similarity	NPC269729
0.8723	High Similarity	NPC103527
0.8652	High Similarity	NPC307258
0.8632	High Similarity	NPC139570
0.8602	High Similarity	NPC85173
0.8571	High Similarity	NPC235341
0.8571	High Similarity	NPC477579
0.8571	High Similarity	NPC158393
0.8571	High Similarity	NPC475862
0.8571	High Similarity	NPC95594
0.8571	High Similarity	NPC74363
0.8557	High Similarity	NPC471966
0.8526	High Similarity	NPC23170
0.8511	High Similarity	NPC272746
0.8511	High Similarity	NPC472978
0.8511	High Similarity	NPC230064
0.8511	High Similarity	NPC4036
0.8511	High Similarity	NPC233455
0.8511	High Similarity	NPC99380
0.8511	High Similarity	NPC158030
0.8511	High Similarity	NPC65120
0.8511	High Similarity	NPC145067
0.8495	Intermediate Similarity	NPC472973
0.8495	Intermediate Similarity	NPC69627
0.8495	Intermediate Similarity	NPC477973
0.8495	Intermediate Similarity	NPC472983
0.8478	Intermediate Similarity	NPC73064
0.8478	Intermediate Similarity	NPC153604
0.8469	Intermediate Similarity	NPC475392
0.8469	Intermediate Similarity	NPC475385
0.8469	Intermediate Similarity	NPC475202
0.8462	Intermediate Similarity	NPC133954
0.8454	Intermediate Similarity	NPC190554
0.8438	Intermediate Similarity	NPC473240
0.8421	Intermediate Similarity	NPC214756
0.8421	Intermediate Similarity	NPC295643
0.8421	Intermediate Similarity	NPC272075
0.8404	Intermediate Similarity	NPC328141
0.8404	Intermediate Similarity	NPC291028
0.8404	Intermediate Similarity	NPC191684
0.8404	Intermediate Similarity	NPC183283
0.84	Intermediate Similarity	NPC478057
0.8387	Intermediate Similarity	NPC473229
0.8387	Intermediate Similarity	NPC328539
0.8387	Intermediate Similarity	NPC158778
0.837	Intermediate Similarity	NPC472985
0.837	Intermediate Similarity	NPC472986
0.837	Intermediate Similarity	NPC213412
0.837	Intermediate Similarity	NPC34190
0.8367	Intermediate Similarity	NPC114274
0.8367	Intermediate Similarity	NPC194196
0.8351	Intermediate Similarity	NPC476318
0.8351	Intermediate Similarity	NPC471039
0.8351	Intermediate Similarity	NPC167193
0.8351	Intermediate Similarity	NPC473158
0.8351	Intermediate Similarity	NPC476327
0.8351	Intermediate Similarity	NPC472806
0.8333	Intermediate Similarity	NPC472977
0.8333	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC245972
0.8333	Intermediate Similarity	NPC474529
0.8333	Intermediate Similarity	NPC470813
0.8333	Intermediate Similarity	NPC111015
0.8333	Intermediate Similarity	NPC472976
0.8316	Intermediate Similarity	NPC185936
0.8316	Intermediate Similarity	NPC105189
0.8316	Intermediate Similarity	NPC472975
0.8316	Intermediate Similarity	NPC168027
0.8298	Intermediate Similarity	NPC275740
0.8298	Intermediate Similarity	NPC119416
0.8298	Intermediate Similarity	NPC186688
0.8298	Intermediate Similarity	NPC86319
0.8283	Intermediate Similarity	NPC15390
0.828	Intermediate Similarity	NPC298904
0.8265	Intermediate Similarity	NPC89225
0.8265	Intermediate Similarity	NPC473456
0.8265	Intermediate Similarity	NPC108078
0.8265	Intermediate Similarity	NPC189880
0.8261	Intermediate Similarity	NPC470574
0.8252	Intermediate Similarity	NPC275539
0.8252	Intermediate Similarity	NPC189075
0.8247	Intermediate Similarity	NPC473170
0.8247	Intermediate Similarity	NPC139459
0.8247	Intermediate Similarity	NPC148523
0.8247	Intermediate Similarity	NPC271195
0.8242	Intermediate Similarity	NPC64600
0.8229	Intermediate Similarity	NPC298554
0.8222	Intermediate Similarity	NPC473217
0.8218	Intermediate Similarity	NPC275583
0.8218	Intermediate Similarity	NPC95899
0.8211	Intermediate Similarity	NPC120968
0.8211	Intermediate Similarity	NPC210037
0.8211	Intermediate Similarity	NPC477872
0.8211	Intermediate Similarity	NPC7260
0.8211	Intermediate Similarity	NPC227467
0.8211	Intermediate Similarity	NPC273621
0.8211	Intermediate Similarity	NPC290614
0.8211	Intermediate Similarity	NPC80401
0.8211	Intermediate Similarity	NPC126993
0.8211	Intermediate Similarity	NPC18872
0.8211	Intermediate Similarity	NPC193750
0.8191	Intermediate Similarity	NPC143767
0.8191	Intermediate Similarity	NPC472739
0.8191	Intermediate Similarity	NPC230387
0.8191	Intermediate Similarity	NPC193360
0.8191	Intermediate Similarity	NPC131470
0.8191	Intermediate Similarity	NPC52169
0.8191	Intermediate Similarity	NPC474677
0.8191	Intermediate Similarity	NPC182797
0.8182	Intermediate Similarity	NPC260149
0.8182	Intermediate Similarity	NPC58942
0.8182	Intermediate Similarity	NPC478056
0.8182	Intermediate Similarity	NPC103051
0.8173	Intermediate Similarity	NPC310546
0.8163	Intermediate Similarity	NPC219353
0.8163	Intermediate Similarity	NPC98874
0.8163	Intermediate Similarity	NPC135548
0.8163	Intermediate Similarity	NPC264979
0.8155	Intermediate Similarity	NPC110496
0.8152	Intermediate Similarity	NPC146683
0.8152	Intermediate Similarity	NPC251170
0.8152	Intermediate Similarity	NPC180834
0.8152	Intermediate Similarity	NPC227132
0.8144	Intermediate Similarity	NPC196227
0.8144	Intermediate Similarity	NPC74751
0.8144	Intermediate Similarity	NPC159365
0.8144	Intermediate Similarity	NPC222047
0.8144	Intermediate Similarity	NPC471040
0.8144	Intermediate Similarity	NPC209868
0.8137	Intermediate Similarity	NPC209502
0.8137	Intermediate Similarity	NPC204833
0.8132	Intermediate Similarity	NPC48362
0.8125	Intermediate Similarity	NPC474525
0.8125	Intermediate Similarity	NPC131872
0.8125	Intermediate Similarity	NPC475708
0.8125	Intermediate Similarity	NPC86266
0.8125	Intermediate Similarity	NPC212301
0.8125	Intermediate Similarity	NPC187722
0.8125	Intermediate Similarity	NPC110657
0.8125	Intermediate Similarity	NPC38754
0.8125	Intermediate Similarity	NPC476168
0.8125	Intermediate Similarity	NPC116726
0.8111	Intermediate Similarity	NPC2482
0.8105	Intermediate Similarity	NPC121798
0.8105	Intermediate Similarity	NPC31985
0.8105	Intermediate Similarity	NPC263393
0.8105	Intermediate Similarity	NPC477943
0.8105	Intermediate Similarity	NPC143232
0.8105	Intermediate Similarity	NPC130520
0.8105	Intermediate Similarity	NPC290972
0.8105	Intermediate Similarity	NPC61543
0.8105	Intermediate Similarity	NPC225585
0.8105	Intermediate Similarity	NPC25906
0.8105	Intermediate Similarity	NPC198664
0.8105	Intermediate Similarity	NPC59263
0.8105	Intermediate Similarity	NPC293048
0.8105	Intermediate Similarity	NPC270768
0.8105	Intermediate Similarity	NPC234346
0.8105	Intermediate Similarity	NPC64872
0.8105	Intermediate Similarity	NPC127689
0.8105	Intermediate Similarity	NPC469546
0.8105	Intermediate Similarity	NPC274330
0.8105	Intermediate Similarity	NPC1015
0.81	Intermediate Similarity	NPC471727
0.81	Intermediate Similarity	NPC154072
0.8085	Intermediate Similarity	NPC293564
0.8085	Intermediate Similarity	NPC88716
0.8085	Intermediate Similarity	NPC142415
0.8085	Intermediate Similarity	NPC93778
0.8085	Intermediate Similarity	NPC242468
0.8085	Intermediate Similarity	NPC171203
0.8085	Intermediate Similarity	NPC307426
0.8085	Intermediate Similarity	NPC259009
0.8085	Intermediate Similarity	NPC51700
0.8085	Intermediate Similarity	NPC18064
0.8085	Intermediate Similarity	NPC68160
0.8085	Intermediate Similarity	NPC98442
0.8085	Intermediate Similarity	NPC174619
0.8085	Intermediate Similarity	NPC102683
0.8085	Intermediate Similarity	NPC475740
0.8085	Intermediate Similarity	NPC130577
0.8081	Intermediate Similarity	NPC273269
0.8081	Intermediate Similarity	NPC43686
0.8081	Intermediate Similarity	NPC187933
0.8077	Intermediate Similarity	NPC476802
0.8077	Intermediate Similarity	NPC89171
0.8061	Intermediate Similarity	NPC142352
0.8061	Intermediate Similarity	NPC41070

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 NPC5532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1802
0.2-0.3	3972
0.3-0.4	2115
0.4-0.5	638
0.5-0.6	193
0.6-0.7	125
0.7-0.8	98
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD4697	Phase 3
0.8511	High Similarity	NPD6079	Approved
0.8511	High Similarity	NPD7515	Phase 2
0.8495	Intermediate Similarity	NPD5328	Approved
0.837	Intermediate Similarity	NPD3618	Phase 1
0.8265	Intermediate Similarity	NPD7902	Approved
0.8163	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD5221	Approved
0.8163	Intermediate Similarity	NPD5222	Approved
0.8144	Intermediate Similarity	NPD7748	Approved
0.8081	Intermediate Similarity	NPD5173	Approved
0.7959	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7900	Approved
0.7921	Intermediate Similarity	NPD5285	Approved
0.7921	Intermediate Similarity	NPD5286	Approved
0.7921	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD4755	Approved
0.7843	Intermediate Similarity	NPD5223	Approved
0.7767	Intermediate Similarity	NPD5224	Approved
0.7767	Intermediate Similarity	NPD5211	Phase 2
0.7767	Intermediate Similarity	NPD4633	Approved
0.7767	Intermediate Similarity	NPD5226	Approved
0.7767	Intermediate Similarity	NPD5225	Approved
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD4786	Approved
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7745	Intermediate Similarity	NPD4700	Approved
0.7742	Intermediate Similarity	NPD3667	Approved
0.7692	Intermediate Similarity	NPD5175	Approved
0.7692	Intermediate Similarity	NPD5174	Approved
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6650	Approved
0.7677	Intermediate Similarity	NPD4202	Approved
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6373	Approved
0.7619	Intermediate Similarity	NPD5141	Approved
0.7604	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4634	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7527	Intermediate Similarity	NPD4695	Discontinued
0.7526	Intermediate Similarity	NPD3573	Approved
0.7524	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7477	Intermediate Similarity	NPD5697	Approved
0.7476	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7419	Intermediate Similarity	NPD7645	Phase 2
0.7407	Intermediate Similarity	NPD4730	Approved
0.7407	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD5168	Approved
0.7407	Intermediate Similarity	NPD4729	Approved
0.7407	Intermediate Similarity	NPD5128	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7387	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD4767	Approved
0.7383	Intermediate Similarity	NPD4768	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5701	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD5247	Approved
0.7273	Intermediate Similarity	NPD5249	Phase 3
0.7273	Intermediate Similarity	NPD5248	Approved
0.7273	Intermediate Similarity	NPD5135	Approved
0.7273	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5251	Approved
0.7273	Intermediate Similarity	NPD5250	Approved
0.7273	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7222	Intermediate Similarity	NPD6008	Approved
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7207	Intermediate Similarity	NPD5217	Approved
0.7207	Intermediate Similarity	NPD5216	Approved
0.7207	Intermediate Similarity	NPD5215	Approved
0.7207	Intermediate Similarity	NPD5127	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6009	Approved
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7158	Intermediate Similarity	NPD7525	Registered
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7113	Intermediate Similarity	NPD4788	Approved
0.7105	Intermediate Similarity	NPD6868	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7048	Intermediate Similarity	NPD6083	Phase 2
0.7048	Intermediate Similarity	NPD6084	Phase 2
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD4197	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7018	Intermediate Similarity	NPD5167	Approved
0.7009	Intermediate Similarity	NPD6319	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6975	Remote Similarity	NPD7604	Phase 2
0.6957	Remote Similarity	NPD6274	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD5983	Phase 2
0.6949	Remote Similarity	NPD6016	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD5205	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4690	Approved
0.69	Remote Similarity	NPD4623	Approved
0.6897	Remote Similarity	NPD6317	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.686	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD6942	Approved
0.6807	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7078	Approved
0.6792	Remote Similarity	NPD7732	Phase 3
0.6789	Remote Similarity	NPD7632	Discontinued
0.6771	Remote Similarity	NPD6118	Approved
0.6771	Remote Similarity	NPD6114	Approved
0.6771	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD6697	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4691	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4694	Approved
0.6733	Remote Similarity	NPD5280	Approved
0.6731	Remote Similarity	NPD5281	Approved
0.6731	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6698	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD6686	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD4137	Phase 3
0.663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3699	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