NPASS Compound

Structure

NPC471207 OpenBabel07101718182D 29 33 0 0 1 0 0 0 0 0999 V2000 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 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 -0.5000 0.0000 C 0 0 0 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 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 0.8660 1.5000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.8660 -1.5000 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 -0.8660 1.5000 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 -1.8171 1.8090 0.0000 C 0 0 0 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 0.8660 0.5000 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 0.0000 -1.0000 0.0000 C 0 0 2 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 0.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 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 23 1 0 0 0 0 2 23 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 24 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 25 1 1 0 0 0 18 28 2 0 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 1 0 0 0 22 29 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 26 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.28
Volume:	433.931
LogP:	4.339
LogD:	3.834
LogS:	-4.85
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	5.048
Fsp3:	0.808
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.796
MDCK Permeability:	2.1950623704469763e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.543
Plasma Protein Binding (PPB):	90.64655303955078%
Volume Distribution (VD):	0.687
Pgp-substrate:	6.19228982925415%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	9.706
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.502
Human Hepatotoxicity (H-HT):	0.472
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.943
Carcinogencity:	0.486
Eye Corrosion:	0.008
Eye Irritation:	0.064
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC471207

Natural Product ID:	NPC471207
*Common Name:**	Rel-12Beta,22-Dihydroxy-24-Oxo-24-Homoscalara-16,25(26)-Diene
IUPAC Name:	(5aS,5bR,7aS,11aR,11bS,13R,13aS,13bR)-13-hydroxy-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydrocyclopenta[a]chrysen-3-one
Synonyms:
Standard InCHIKey:	SCQWNYQIOKUMKH-AJSCXSSXSA-N
Standard InCHI:	InChI=1S/C26H38O3/c1-23(2)11-5-12-26(15-27)19(23)10-13-24(3)20-9-6-16-17(7-8-18(16)28)25(20,4)22(29)14-21(24)26/h6-8,17,19-22,27,29H,5,9-15H2,1-4H3/t17-,19-,20-,21-,22+,24-,25+,26+/m0/s1
SMILES:	OC[C@@]12CCCC([C@@H]2CC[C@@]2([C@@H]1C[C@@H](O)[C@]1([C@H]2CC=C2[C@@H]1C=CC2=O)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387626
PubChem CID:	71658747
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	=	4170.0	nM	PMID[519186]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	4500.0	nM	PMID[519186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5280.0	nM	PMID[519186]

☑ 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 NPC471207 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	193
0.1-0.2	1276
0.2-0.3	4717
0.3-0.4	10687
0.4-0.5	12078
0.5-0.6	6234
0.6-0.7	5188
0.7-0.8	2081
0.8-0.85	211
0.85-0.9	25
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC85173
0.913	High Similarity	NPC469545
0.913	High Similarity	NPC5532
0.913	High Similarity	NPC61369
0.9111	High Similarity	NPC272746
0.8989	High Similarity	NPC474925
0.8791	High Similarity	NPC126993
0.8778	High Similarity	NPC328539
0.8778	High Similarity	NPC158778
0.8778	High Similarity	NPC472802
0.8778	High Similarity	NPC206060
0.8764	High Similarity	NPC158393
0.8737	High Similarity	NPC114274
0.8696	High Similarity	NPC131872
0.8681	High Similarity	NPC472973
0.8681	High Similarity	NPC69627
0.8681	High Similarity	NPC275740
0.8681	High Similarity	NPC186688
0.8681	High Similarity	NPC119416
0.8681	High Similarity	NPC86319
0.8667	High Similarity	NPC298904
0.8667	High Similarity	NPC93778
0.8652	High Similarity	NPC470574
0.8652	High Similarity	NPC133954
0.8632	High Similarity	NPC190554
0.8632	High Similarity	NPC108078
0.8617	High Similarity	NPC473170
0.8617	High Similarity	NPC139570
0.8571	High Similarity	NPC282233
0.8571	High Similarity	NPC95585
0.8571	High Similarity	NPC193360
0.8571	High Similarity	NPC131470
0.8571	High Similarity	NPC143767
0.8571	High Similarity	NPC474677
0.8556	High Similarity	NPC213412
0.8556	High Similarity	NPC475862
0.8556	High Similarity	NPC471737
0.8556	High Similarity	NPC74363
0.8556	High Similarity	NPC472985
0.8556	High Similarity	NPC472986
0.8542	High Similarity	NPC103051
0.8526	High Similarity	NPC473158
0.8511	High Similarity	NPC103527
0.8511	High Similarity	NPC23170
0.8511	High Similarity	NPC245972
0.8511	High Similarity	NPC111015
0.8511	High Similarity	NPC196485
0.8495	Intermediate Similarity	NPC4036
0.8495	Intermediate Similarity	NPC185936
0.8495	Intermediate Similarity	NPC168027
0.8495	Intermediate Similarity	NPC472978
0.8495	Intermediate Similarity	NPC233455
0.8495	Intermediate Similarity	NPC472975
0.8495	Intermediate Similarity	NPC158030
0.8495	Intermediate Similarity	NPC145067
0.8495	Intermediate Similarity	NPC65120
0.8462	Intermediate Similarity	NPC141292
0.8462	Intermediate Similarity	NPC475740
0.8462	Intermediate Similarity	NPC73064
0.8462	Intermediate Similarity	NPC58063
0.8462	Intermediate Similarity	NPC153604
0.8454	Intermediate Similarity	NPC15390
0.8438	Intermediate Similarity	NPC473456
0.8427	Intermediate Similarity	NPC64600
0.8421	Intermediate Similarity	NPC473240
0.8421	Intermediate Similarity	NPC271195
0.8421	Intermediate Similarity	NPC259286
0.8409	Intermediate Similarity	NPC473217
0.8404	Intermediate Similarity	NPC134826
0.8404	Intermediate Similarity	NPC214756
0.8404	Intermediate Similarity	NPC295643
0.8404	Intermediate Similarity	NPC272075
0.8404	Intermediate Similarity	NPC69454
0.8387	Intermediate Similarity	NPC191684
0.8387	Intermediate Similarity	NPC183283
0.837	Intermediate Similarity	NPC471722
0.837	Intermediate Similarity	NPC310752
0.837	Intermediate Similarity	NPC292491
0.8352	Intermediate Similarity	NPC474732
0.8352	Intermediate Similarity	NPC145879
0.8352	Intermediate Similarity	NPC31564
0.8352	Intermediate Similarity	NPC477579
0.8352	Intermediate Similarity	NPC72133
0.8352	Intermediate Similarity	NPC474733
0.8352	Intermediate Similarity	NPC235341
0.8352	Intermediate Similarity	NPC95594
0.8352	Intermediate Similarity	NPC474778
0.8333	Intermediate Similarity	NPC214043
0.8333	Intermediate Similarity	NPC476318
0.8333	Intermediate Similarity	NPC227132
0.8333	Intermediate Similarity	NPC471039
0.8333	Intermediate Similarity	NPC146683
0.8333	Intermediate Similarity	NPC249954
0.8333	Intermediate Similarity	NPC476327
0.8333	Intermediate Similarity	NPC180834
0.8333	Intermediate Similarity	NPC85774
0.8317	Intermediate Similarity	NPC110496
0.8316	Intermediate Similarity	NPC472977
0.8316	Intermediate Similarity	NPC474529
0.8316	Intermediate Similarity	NPC473172
0.8316	Intermediate Similarity	NPC472976
0.8316	Intermediate Similarity	NPC209662
0.8315	Intermediate Similarity	NPC48362
0.8298	Intermediate Similarity	NPC63748
0.8298	Intermediate Similarity	NPC475806
0.8298	Intermediate Similarity	NPC233116
0.8295	Intermediate Similarity	NPC2482
0.8295	Intermediate Similarity	NPC476809
0.828	Intermediate Similarity	NPC184663
0.828	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC473999
0.828	Intermediate Similarity	NPC309603
0.828	Intermediate Similarity	NPC31985
0.8265	Intermediate Similarity	NPC471041
0.8265	Intermediate Similarity	NPC144956
0.8261	Intermediate Similarity	NPC130577
0.8261	Intermediate Similarity	NPC68160
0.8261	Intermediate Similarity	NPC18064
0.8261	Intermediate Similarity	NPC98442
0.8261	Intermediate Similarity	NPC171203
0.8261	Intermediate Similarity	NPC142415
0.8261	Intermediate Similarity	NPC51700
0.8261	Intermediate Similarity	NPC307426
0.8261	Intermediate Similarity	NPC88716
0.8261	Intermediate Similarity	NPC259009
0.8261	Intermediate Similarity	NPC102683
0.8261	Intermediate Similarity	NPC242468
0.8261	Intermediate Similarity	NPC293564
0.8252	Intermediate Similarity	NPC197428
0.8247	Intermediate Similarity	NPC189880
0.8242	Intermediate Similarity	NPC190704
0.8242	Intermediate Similarity	NPC469948
0.8242	Intermediate Similarity	NPC471034
0.8242	Intermediate Similarity	NPC476426
0.8235	Intermediate Similarity	NPC275539
0.8235	Intermediate Similarity	NPC189075
0.8229	Intermediate Similarity	NPC148523
0.8229	Intermediate Similarity	NPC280725
0.8229	Intermediate Similarity	NPC139459
0.8222	Intermediate Similarity	NPC118800
0.8222	Intermediate Similarity	NPC307258
0.8211	Intermediate Similarity	NPC79117
0.8211	Intermediate Similarity	NPC475255
0.8211	Intermediate Similarity	NPC12722
0.8211	Intermediate Similarity	NPC477855
0.8202	Intermediate Similarity	NPC3915
0.82	Intermediate Similarity	NPC312900
0.82	Intermediate Similarity	NPC264048
0.82	Intermediate Similarity	NPC478057
0.82	Intermediate Similarity	NPC95899
0.8191	Intermediate Similarity	NPC48010
0.8191	Intermediate Similarity	NPC80401
0.8191	Intermediate Similarity	NPC291028
0.8191	Intermediate Similarity	NPC328141
0.8172	Intermediate Similarity	NPC246708
0.8172	Intermediate Similarity	NPC40552
0.8172	Intermediate Similarity	NPC470629
0.8172	Intermediate Similarity	NPC471724
0.8172	Intermediate Similarity	NPC290690
0.8172	Intermediate Similarity	NPC473242
0.8172	Intermediate Similarity	NPC182797
0.8172	Intermediate Similarity	NPC230387
0.8172	Intermediate Similarity	NPC52169
0.8172	Intermediate Similarity	NPC53911
0.8172	Intermediate Similarity	NPC17733
0.8172	Intermediate Similarity	NPC474512
0.8172	Intermediate Similarity	NPC181225
0.8163	Intermediate Similarity	NPC58942
0.8163	Intermediate Similarity	NPC194196
0.8163	Intermediate Similarity	NPC260149
0.8161	Intermediate Similarity	NPC472746
0.8161	Intermediate Similarity	NPC197659
0.8152	Intermediate Similarity	NPC222613
0.8152	Intermediate Similarity	NPC118648
0.8152	Intermediate Similarity	NPC72638
0.8152	Intermediate Similarity	NPC327115
0.8152	Intermediate Similarity	NPC94666
0.8152	Intermediate Similarity	NPC475022
0.8152	Intermediate Similarity	NPC194417
0.8144	Intermediate Similarity	NPC98874
0.8144	Intermediate Similarity	NPC192428
0.8144	Intermediate Similarity	NPC472806
0.8144	Intermediate Similarity	NPC473164
0.8144	Intermediate Similarity	NPC167193
0.8132	Intermediate Similarity	NPC473246
0.8132	Intermediate Similarity	NPC251170
0.8132	Intermediate Similarity	NPC33913
0.8132	Intermediate Similarity	NPC59453
0.8132	Intermediate Similarity	NPC161423
0.8132	Intermediate Similarity	NPC472265
0.8132	Intermediate Similarity	NPC227064
0.8132	Intermediate Similarity	NPC221758
0.8132	Intermediate Similarity	NPC470812
0.8132	Intermediate Similarity	NPC476412
0.8132	Intermediate Similarity	NPC329043
0.8132	Intermediate Similarity	NPC321187
0.8132	Intermediate Similarity	NPC58841
0.8125	Intermediate Similarity	NPC74751
0.8125	Intermediate Similarity	NPC8993
0.8125	Intermediate Similarity	NPC471040

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 NPC471207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1574
0.2-0.3	3948
0.3-0.4	2302
0.4-0.5	707
0.5-0.6	166
0.6-0.7	149
0.7-0.8	119
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9111	High Similarity	NPD6079	Approved
0.8889	High Similarity	NPD5328	Approved
0.8556	High Similarity	NPD3618	Phase 1
0.8526	High Similarity	NPD5221	Approved
0.8526	High Similarity	NPD5220	Clinical (unspecified phase)
0.8526	High Similarity	NPD5222	Approved
0.8495	Intermediate Similarity	NPD7515	Phase 2
0.8438	Intermediate Similarity	NPD5173	Approved
0.8265	Intermediate Similarity	NPD4696	Approved
0.8265	Intermediate Similarity	NPD5286	Approved
0.8265	Intermediate Similarity	NPD5285	Approved
0.8182	Intermediate Similarity	NPD5223	Approved
0.8144	Intermediate Similarity	NPD4697	Phase 3
0.8132	Intermediate Similarity	NPD3665	Phase 1
0.8132	Intermediate Similarity	NPD4786	Approved
0.8132	Intermediate Similarity	NPD3133	Approved
0.8132	Intermediate Similarity	NPD3666	Approved
0.8125	Intermediate Similarity	NPD7748	Approved
0.8111	Intermediate Similarity	NPD3667	Approved
0.81	Intermediate Similarity	NPD4633	Approved
0.81	Intermediate Similarity	NPD5225	Approved
0.81	Intermediate Similarity	NPD5224	Approved
0.81	Intermediate Similarity	NPD5226	Approved
0.81	Intermediate Similarity	NPD5211	Phase 2
0.8061	Intermediate Similarity	NPD4755	Approved
0.8021	Intermediate Similarity	NPD4202	Approved
0.802	Intermediate Similarity	NPD5175	Approved
0.802	Intermediate Similarity	NPD5174	Approved
0.7941	Intermediate Similarity	NPD5141	Approved
0.7905	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD4700	Approved
0.7885	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD6881	Approved
0.7879	Intermediate Similarity	NPD7902	Approved
0.7872	Intermediate Similarity	NPD3573	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7736	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD6883	Approved
0.7736	Intermediate Similarity	NPD7290	Approved
0.7714	Intermediate Similarity	NPD5168	Approved
0.7714	Intermediate Similarity	NPD4730	Approved
0.7714	Intermediate Similarity	NPD4729	Approved
0.7714	Intermediate Similarity	NPD6011	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7685	Intermediate Similarity	NPD4632	Approved
0.767	Intermediate Similarity	NPD4754	Approved
0.7664	Intermediate Similarity	NPD6847	Approved
0.7664	Intermediate Similarity	NPD6649	Approved
0.7664	Intermediate Similarity	NPD6617	Approved
0.7664	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6869	Approved
0.766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD6012	Approved
0.7642	Intermediate Similarity	NPD6013	Approved
0.7624	Intermediate Similarity	NPD7638	Approved
0.7604	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6882	Approved
0.7593	Intermediate Similarity	NPD8297	Approved
0.7582	Intermediate Similarity	NPD7645	Phase 2
0.7579	Intermediate Similarity	NPD4623	Approved
0.7579	Intermediate Similarity	NPD5279	Phase 3
0.7579	Intermediate Similarity	NPD4519	Discontinued
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7900	Approved
0.757	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5135	Approved
0.757	Intermediate Similarity	NPD5169	Approved
0.757	Intermediate Similarity	NPD5251	Approved
0.757	Intermediate Similarity	NPD5250	Approved
0.757	Intermediate Similarity	NPD5247	Approved
0.757	Intermediate Similarity	NPD5248	Approved
0.757	Intermediate Similarity	NPD5249	Phase 3
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD5128	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7528	Intermediate Similarity	NPD3703	Phase 2
0.7527	Intermediate Similarity	NPD4223	Phase 3
0.7527	Intermediate Similarity	NPD4221	Approved
0.7526	Intermediate Similarity	NPD4753	Phase 2
0.7524	Intermediate Similarity	NPD4767	Approved
0.7524	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD5210	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6009	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7474	Intermediate Similarity	NPD5329	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7447	Intermediate Similarity	NPD4788	Approved
0.7434	Intermediate Similarity	NPD6054	Approved
0.7396	Intermediate Similarity	NPD6684	Approved
0.7396	Intermediate Similarity	NPD5330	Approved
0.7396	Intermediate Similarity	NPD7521	Approved
0.7396	Intermediate Similarity	NPD5690	Phase 2
0.7396	Intermediate Similarity	NPD7146	Approved
0.7396	Intermediate Similarity	NPD6409	Approved
0.7396	Intermediate Similarity	NPD7334	Approved
0.7387	Intermediate Similarity	NPD6868	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD4197	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7525	Registered
0.7304	Intermediate Similarity	NPD6370	Approved
0.73	Intermediate Similarity	NPD6399	Phase 3
0.7297	Intermediate Similarity	NPD5167	Approved
0.729	Intermediate Similarity	NPD6412	Phase 2
0.7288	Intermediate Similarity	NPD7736	Approved
0.7283	Intermediate Similarity	NPD3617	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD6335	Approved
0.7245	Intermediate Similarity	NPD6903	Approved
0.7241	Intermediate Similarity	NPD7604	Phase 2
0.7217	Intermediate Similarity	NPD6016	Approved
0.7217	Intermediate Similarity	NPD6015	Approved
0.7217	Intermediate Similarity	NPD5983	Phase 2
0.7216	Intermediate Similarity	NPD4690	Approved
0.7216	Intermediate Similarity	NPD4689	Approved
0.7216	Intermediate Similarity	NPD4688	Approved
0.7216	Intermediate Similarity	NPD4138	Approved
0.7216	Intermediate Similarity	NPD4693	Phase 3
0.7216	Intermediate Similarity	NPD5205	Approved
0.7204	Intermediate Similarity	NPD4195	Approved
0.7196	Intermediate Similarity	NPD6008	Approved
0.7193	Intermediate Similarity	NPD7101	Approved
0.7193	Intermediate Similarity	NPD7100	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD7492	Approved
0.7172	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6317	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7155	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.713	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD6336	Discontinued
0.7119	Intermediate Similarity	NPD6616	Approved
0.7115	Intermediate Similarity	NPD5290	Discontinued
0.7105	Intermediate Similarity	NPD6313	Approved
0.7105	Intermediate Similarity	NPD6314	Approved
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.708	Intermediate Similarity	NPD6274	Approved
0.7079	Intermediate Similarity	NPD4691	Approved
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7065	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7078	Approved
0.7041	Intermediate Similarity	NPD5280	Approved
0.7041	Intermediate Similarity	NPD4694	Approved
0.7033	Intermediate Similarity	NPD4058	Approved
0.703	Intermediate Similarity	NPD8035	Phase 2
0.703	Intermediate Similarity	NPD8034	Phase 2
0.703	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4137	Phase 3
0.6966	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1694	Approved
0.6939	Remote Similarity	NPD1696	Phase 3
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7632	Discontinued
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD4747	Approved
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.6833	Remote Similarity	NPD7507	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7331	Phase 2
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD6908	Approved
0.6777	Remote Similarity	NPD8293	Discontinued
0.6762	Remote Similarity	NPD7732	Phase 3
0.6757	Remote Similarity	NPD6686	Approved
0.6721	Remote Similarity	NPD6033	Approved
0.6705	Remote Similarity	NPD7341	Phase 2
0.6703	Remote Similarity	NPD4244	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