NPASS Compound

Structure

NPC474668 OpenBabel07101719252D 33 36 0 0 1 0 0 0 0 0999 V2000 2.0345 2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0042 4.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2037 3.1805 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.9292 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -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 4.3301 -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 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 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 0.0000 C 0 0 0 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 -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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7473 3.4895 0.0000 C 0 0 0 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 4.2327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 8 1 0 0 0 0 8 20 2 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 7 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 6 0 0 0 19 26 1 6 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 6 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 1 0 0 0 24 31 1 6 0 0 0 25 32 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.33
Volume:	497.296
LogP:	3.416
LogD:	2.962
LogS:	-3.289
# 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:	5.132
Fsp3:	0.857
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:	-4.745
MDCK Permeability:	1.2872446859546471e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.225
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.533
Plasma Protein Binding (PPB):	76.54762268066406%
Volume Distribution (VD):	0.963
Pgp-substrate:	12.310860633850098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.424
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	7.014
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.532
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.44
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC474668

Natural Product ID:	NPC474668
*Common Name:**	(3Beta,4Beta,22R)-Ergosta-5,24(24')-Diene-3,4,22-Triol
IUPAC Name:	(2S,3S)-2-[(3S,4R,8S,9S,10R,13S,14S,17S)-3,4-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptane-2,3,6-triol
Synonyms:
Standard InCHIKey:	RDGFOCPOKUUIFP-FLMXEVAOSA-N
Standard InCHI:	InChI=1S/C28H46O5/c1-16(25(2,3)32)15-23(30)28(6,33)22-10-9-18-17-7-8-20-24(31)21(29)12-14-26(20,4)19(17)11-13-27(18,22)5/h8,17-19,21-24,29-33H,1,7,9-15H2,2-6H3/t17-,18-,19-,21-,22-,23-,24+,26+,27-,28-/m0/s1
SMILES:	CC12CCC3C(C1CCC2C(C)(C(CC(=C)C(C)(C)O)O)O)CC=C4C3(CCC(C4O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478809
PubChem CID:	44575597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0002198] Pentahydroxy bile acids, alcohols 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
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves	n.a.	n.a.	PMID[15043407]
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	EC50	>	1000.0	nM	PMID[488341]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	1.0	10'3nM	PMID[488341]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	1.0	10'3nM	PMID[488341]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	1.0	10'3nM	PMID[488341]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	1.0	10'3nM	PMID[488341]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	1.0	10'3nM	PMID[488341]

☑ 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 NPC474668 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	173
0.1-0.2	1384
0.2-0.3	4921
0.3-0.4	13499
0.4-0.5	9709
0.5-0.6	5909
0.6-0.7	5233
0.7-0.8	1510
0.8-0.85	256
0.85-0.9	79
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC133588
0.9419	High Similarity	NPC97404
0.9419	High Similarity	NPC41554
0.9412	High Similarity	NPC470361
0.939	High Similarity	NPC317458
0.939	High Similarity	NPC474634
0.9302	High Similarity	NPC80561
0.9302	High Similarity	NPC329596
0.9302	High Similarity	NPC204188
0.9302	High Similarity	NPC3345
0.9302	High Similarity	NPC11216
0.9302	High Similarity	NPC291484
0.9286	High Similarity	NPC261266
0.9286	High Similarity	NPC6391
0.9146	High Similarity	NPC209620
0.9146	High Similarity	NPC23852
0.907	High Similarity	NPC280556
0.9059	High Similarity	NPC293287
0.9059	High Similarity	NPC152808
0.9059	High Similarity	NPC94462
0.9048	High Similarity	NPC185568
0.9036	High Similarity	NPC50964
0.9	High Similarity	NPC72204
0.9	High Similarity	NPC288970
0.8989	High Similarity	NPC477605
0.8966	High Similarity	NPC105495
0.8966	High Similarity	NPC477606
0.8953	High Similarity	NPC470620
0.8929	High Similarity	NPC207013
0.8916	High Similarity	NPC264245
0.8916	High Similarity	NPC474531
0.8902	High Similarity	NPC81306
0.8902	High Similarity	NPC143182
0.8902	High Similarity	NPC47982
0.8902	High Similarity	NPC328714
0.8902	High Similarity	NPC84694
0.8902	High Similarity	NPC30986
0.8902	High Similarity	NPC209430
0.8902	High Similarity	NPC109546
0.8902	High Similarity	NPC28862
0.8876	High Similarity	NPC310013
0.8864	High Similarity	NPC295668
0.8851	High Similarity	NPC67872
0.8837	High Similarity	NPC299068
0.8824	High Similarity	NPC205845
0.8824	High Similarity	NPC124172
0.881	High Similarity	NPC101462
0.881	High Similarity	NPC30166
0.881	High Similarity	NPC49964
0.881	High Similarity	NPC1272
0.881	High Similarity	NPC7988
0.881	High Similarity	NPC470614
0.8795	High Similarity	NPC209944
0.8795	High Similarity	NPC164840
0.8795	High Similarity	NPC234193
0.8795	High Similarity	NPC236112
0.8795	High Similarity	NPC241290
0.878	High Similarity	NPC474216
0.878	High Similarity	NPC87604
0.8778	High Similarity	NPC127718
0.8778	High Similarity	NPC65402
0.8764	High Similarity	NPC275671
0.8721	High Similarity	NPC470360
0.8706	High Similarity	NPC475789
0.8696	High Similarity	NPC476893
0.869	High Similarity	NPC47761
0.869	High Similarity	NPC476646
0.8681	High Similarity	NPC8774
0.8681	High Similarity	NPC476894
0.8659	High Similarity	NPC155986
0.8659	High Similarity	NPC198968
0.8659	High Similarity	NPC318495
0.8652	High Similarity	NPC473956
0.8652	High Similarity	NPC475751
0.8636	High Similarity	NPC475664
0.8621	High Similarity	NPC139724
0.8621	High Similarity	NPC477604
0.8621	High Similarity	NPC24277
0.8605	High Similarity	NPC238485
0.8605	High Similarity	NPC474047
0.8602	High Similarity	NPC476895
0.8588	High Similarity	NPC87489
0.8588	High Similarity	NPC296701
0.8588	High Similarity	NPC218616
0.8588	High Similarity	NPC189972
0.8587	High Similarity	NPC12103
0.8587	High Similarity	NPC227583
0.8587	High Similarity	NPC103165
0.8587	High Similarity	NPC98457
0.8587	High Similarity	NPC210717
0.8571	High Similarity	NPC322313
0.8571	High Similarity	NPC96362
0.8571	High Similarity	NPC102253
0.8571	High Similarity	NPC287749
0.8571	High Similarity	NPC236237
0.8571	High Similarity	NPC22403
0.8571	High Similarity	NPC26117
0.8571	High Similarity	NPC13554
0.8556	High Similarity	NPC210268
0.8554	High Similarity	NPC167891
0.8554	High Similarity	NPC473943
0.8554	High Similarity	NPC83351
0.8539	High Similarity	NPC187785
0.8539	High Similarity	NPC259875
0.8539	High Similarity	NPC109744
0.8537	High Similarity	NPC321381
0.8537	High Similarity	NPC247325
0.8537	High Similarity	NPC244488
0.8537	High Similarity	NPC274079
0.8537	High Similarity	NPC477925
0.8537	High Similarity	NPC107059
0.8537	High Similarity	NPC321016
0.8523	High Similarity	NPC186145
0.8523	High Similarity	NPC474657
0.8523	High Similarity	NPC149224
0.8506	High Similarity	NPC274448
0.8506	High Similarity	NPC318390
0.8506	High Similarity	NPC266511
0.8495	Intermediate Similarity	NPC261807
0.8495	Intermediate Similarity	NPC477226
0.8488	Intermediate Similarity	NPC211135
0.8488	Intermediate Similarity	NPC320548
0.8488	Intermediate Similarity	NPC216420
0.8488	Intermediate Similarity	NPC85095
0.8488	Intermediate Similarity	NPC110778
0.8471	Intermediate Similarity	NPC474759
0.8471	Intermediate Similarity	NPC474683
0.8471	Intermediate Similarity	NPC470383
0.8471	Intermediate Similarity	NPC474752
0.8471	Intermediate Similarity	NPC474731
0.8471	Intermediate Similarity	NPC7505
0.8471	Intermediate Similarity	NPC82986
0.8462	Intermediate Similarity	NPC98193
0.8454	Intermediate Similarity	NPC166607
0.8452	Intermediate Similarity	NPC80530
0.8452	Intermediate Similarity	NPC273410
0.8444	Intermediate Similarity	NPC107189
0.8444	Intermediate Similarity	NPC470390
0.8444	Intermediate Similarity	NPC270511
0.8444	Intermediate Similarity	NPC14380
0.8444	Intermediate Similarity	NPC192437
0.8444	Intermediate Similarity	NPC245410
0.8434	Intermediate Similarity	NPC130136
0.8427	Intermediate Similarity	NPC470542
0.8421	Intermediate Similarity	NPC476896
0.8421	Intermediate Similarity	NPC475617
0.8415	Intermediate Similarity	NPC230301
0.8415	Intermediate Similarity	NPC304309
0.8415	Intermediate Similarity	NPC285893
0.8415	Intermediate Similarity	NPC162742
0.8415	Intermediate Similarity	NPC288035
0.8415	Intermediate Similarity	NPC141071
0.8415	Intermediate Similarity	NPC134847
0.8415	Intermediate Similarity	NPC22105
0.8415	Intermediate Similarity	NPC136188
0.8415	Intermediate Similarity	NPC471723
0.8415	Intermediate Similarity	NPC28657
0.8415	Intermediate Similarity	NPC257347
0.8409	Intermediate Similarity	NPC121981
0.8409	Intermediate Similarity	NPC71520
0.8409	Intermediate Similarity	NPC269058
0.8409	Intermediate Similarity	NPC201273
0.8409	Intermediate Similarity	NPC237344
0.8391	Intermediate Similarity	NPC475798
0.8391	Intermediate Similarity	NPC470077
0.8391	Intermediate Similarity	NPC127606
0.8391	Intermediate Similarity	NPC255882
0.8391	Intermediate Similarity	NPC209802
0.8391	Intermediate Similarity	NPC231310
0.8372	Intermediate Similarity	NPC470049
0.8372	Intermediate Similarity	NPC248886
0.8372	Intermediate Similarity	NPC202389
0.837	Intermediate Similarity	NPC119562
0.837	Intermediate Similarity	NPC279410
0.8367	Intermediate Similarity	NPC475060
0.8367	Intermediate Similarity	NPC220229
0.8352	Intermediate Similarity	NPC114389
0.8351	Intermediate Similarity	NPC160843
0.8351	Intermediate Similarity	NPC473543
0.8333	Intermediate Similarity	NPC6978
0.8333	Intermediate Similarity	NPC138621
0.8333	Intermediate Similarity	NPC101886
0.8333	Intermediate Similarity	NPC244385
0.8333	Intermediate Similarity	NPC275910
0.8333	Intermediate Similarity	NPC301707
0.8333	Intermediate Similarity	NPC285761
0.8333	Intermediate Similarity	NPC477522
0.8333	Intermediate Similarity	NPC167037
0.8316	Intermediate Similarity	NPC473510
0.8315	Intermediate Similarity	NPC271967
0.8315	Intermediate Similarity	NPC476948
0.8313	Intermediate Similarity	NPC129165
0.8313	Intermediate Similarity	NPC240604
0.8313	Intermediate Similarity	NPC189883
0.8313	Intermediate Similarity	NPC300324
0.8313	Intermediate Similarity	NPC253190
0.8313	Intermediate Similarity	NPC134330
0.8313	Intermediate Similarity	NPC113733
0.8298	Intermediate Similarity	NPC475033
0.8298	Intermediate Similarity	NPC475032

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 NPC474668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1602
0.2-0.3	4164
0.3-0.4	2218
0.4-0.5	556
0.5-0.6	182
0.6-0.7	185
0.7-0.8	71
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7525	Registered
0.8523	High Similarity	NPD4751	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7339	Approved
0.8415	Intermediate Similarity	NPD6942	Approved
0.8315	Intermediate Similarity	NPD7524	Approved
0.8182	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6931	Approved
0.814	Intermediate Similarity	NPD6930	Phase 2
0.8095	Intermediate Similarity	NPD6933	Approved
0.8095	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6695	Phase 3
0.8023	Intermediate Similarity	NPD6929	Approved
0.7931	Intermediate Similarity	NPD7514	Phase 3
0.7857	Intermediate Similarity	NPD6924	Approved
0.7857	Intermediate Similarity	NPD6926	Approved
0.7791	Intermediate Similarity	NPD5776	Phase 2
0.7791	Intermediate Similarity	NPD6925	Approved
0.7778	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD7332	Phase 2
0.7717	Intermediate Similarity	NPD7750	Discontinued
0.7701	Intermediate Similarity	NPD7145	Approved
0.7692	Intermediate Similarity	NPD6893	Approved
0.7647	Intermediate Similarity	NPD4785	Approved
0.7647	Intermediate Similarity	NPD4784	Approved
0.764	Intermediate Similarity	NPD6902	Approved
0.7619	Intermediate Similarity	NPD4243	Approved
0.7586	Intermediate Similarity	NPD6932	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7528	Intermediate Similarity	NPD7509	Discontinued
0.7528	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6898	Phase 1
0.7416	Intermediate Similarity	NPD6683	Phase 2
0.7416	Intermediate Similarity	NPD7645	Phase 2
0.7412	Intermediate Similarity	NPD7150	Approved
0.7412	Intermediate Similarity	NPD7152	Approved
0.7412	Intermediate Similarity	NPD7151	Approved
0.74	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD7087	Discontinued
0.7381	Intermediate Similarity	NPD6923	Approved
0.7381	Intermediate Similarity	NPD6922	Approved
0.7368	Intermediate Similarity	NPD5328	Approved
0.7356	Intermediate Similarity	NPD8264	Approved
0.732	Intermediate Similarity	NPD6399	Phase 3
0.732	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD7638	Approved
0.7294	Intermediate Similarity	NPD7143	Approved
0.7294	Intermediate Similarity	NPD7144	Approved
0.7255	Intermediate Similarity	NPD5211	Phase 2
0.7234	Intermediate Similarity	NPD3618	Phase 1
0.7216	Intermediate Similarity	NPD6079	Approved
0.72	Intermediate Similarity	NPD4755	Approved
0.7176	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5275	Approved
0.7159	Intermediate Similarity	NPD4190	Phase 3
0.7115	Intermediate Similarity	NPD5141	Approved
0.7103	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD5286	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD4696	Approved
0.7054	Intermediate Similarity	NPD7516	Approved
0.7041	Intermediate Similarity	NPD7637	Suspended
0.7033	Intermediate Similarity	NPD4195	Approved
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD3668	Phase 3
0.7021	Intermediate Similarity	NPD3133	Approved
0.7021	Intermediate Similarity	NPD3666	Approved
0.7021	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD6051	Approved
0.701	Intermediate Similarity	NPD4753	Phase 2
0.699	Remote Similarity	NPD4159	Approved
0.699	Remote Similarity	NPD5223	Approved
0.6964	Remote Similarity	NPD7327	Approved
0.6964	Remote Similarity	NPD7328	Approved
0.6931	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5222	Approved
0.6931	Remote Similarity	NPD4697	Phase 3
0.6931	Remote Similarity	NPD5221	Approved
0.693	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6887	Remote Similarity	NPD5739	Approved
0.6887	Remote Similarity	NPD6402	Approved
0.6887	Remote Similarity	NPD7128	Approved
0.6887	Remote Similarity	NPD6675	Approved
0.6863	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD5174	Approved
0.6857	Remote Similarity	NPD4754	Approved
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6809	Remote Similarity	NPD4223	Phase 3
0.6809	Remote Similarity	NPD4221	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6783	Remote Similarity	NPD7503	Approved
0.6771	Remote Similarity	NPD5329	Approved
0.6771	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7136	Phase 2
0.6762	Remote Similarity	NPD7632	Discontinued
0.6759	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD6881	Approved
0.6759	Remote Similarity	NPD7320	Approved
0.6747	Remote Similarity	NPD368	Approved
0.6729	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD4768	Approved
0.6701	Remote Similarity	NPD5279	Phase 3
0.67	Remote Similarity	NPD7515	Phase 2
0.6699	Remote Similarity	NPD6083	Phase 2
0.6699	Remote Similarity	NPD6084	Phase 2
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6373	Approved
0.6697	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6011	Approved
0.6606	Remote Similarity	NPD4730	Approved
0.6606	Remote Similarity	NPD5128	Approved
0.6606	Remote Similarity	NPD4729	Approved
0.6579	Remote Similarity	NPD6009	Approved
0.6577	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6869	Approved
0.6577	Remote Similarity	NPD6847	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6577	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD6640	Phase 3
0.6574	Remote Similarity	NPD6008	Approved
0.6562	Remote Similarity	NPD4788	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5205	Approved
0.6531	Remote Similarity	NPD4690	Approved
0.6531	Remote Similarity	NPD4519	Discontinued
0.6531	Remote Similarity	NPD4623	Approved
0.6531	Remote Similarity	NPD4138	Approved
0.6531	Remote Similarity	NPD4689	Approved
0.6531	Remote Similarity	NPD4693	Phase 3
0.6531	Remote Similarity	NPD4688	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.6486	Remote Similarity	NPD5169	Approved
0.6486	Remote Similarity	NPD5250	Approved
0.6486	Remote Similarity	NPD5248	Approved
0.6486	Remote Similarity	NPD5135	Approved
0.6486	Remote Similarity	NPD5251	Approved
0.6486	Remote Similarity	NPD5249	Phase 3
0.6486	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5290	Discontinued
0.6455	Remote Similarity	NPD6686	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD5215	Approved
0.6429	Remote Similarity	NPD5127	Approved
0.6429	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD5216	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6408	Remote Similarity	NPD7748	Approved
0.64	Remote Similarity	NPD4723	Approved
0.64	Remote Similarity	NPD4722	Approved
0.64	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD6672	Approved
0.6393	Remote Similarity	NPD7319	Approved
0.6387	Remote Similarity	NPD7604	Phase 2
0.6383	Remote Similarity	NPD6115	Approved
0.6383	Remote Similarity	NPD6118	Approved
0.6383	Remote Similarity	NPD6697	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD7902	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