NPASS Compound

Structure

NPC56588 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.7570 -3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3880 -3.3827 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 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -3.0000 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 -3.4641 -1.0000 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 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 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 -0.8660 -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 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2321 2.8660 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.0000 -1.0000 0.0000 C 0 0 1 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 -5.1962 -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 1.7321 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 20 28 1 1 0 0 0 21 26 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	4.456
LogD:	3.375
LogS:	-4.461
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	5.019
Fsp3:	0.867
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:	-5.429
MDCK Permeability:	1.1703852578648366e-05
Pgp-inhibitor:	0.354
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	91.35873413085938%
Volume Distribution (VD):	0.798
Pgp-substrate:	3.0931859016418457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.75
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.584

ADMET: Excretion

Clearance (CL):	2.298
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.64
Skin Sensitization:	0.041
Carcinogencity:	0.131
Eye Corrosion:	0.029
Eye Irritation:	0.176
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC56588

Natural Product ID:	NPC56588
*Common Name:**	Sandorinic Acid C
IUPAC Name:	(2R,4aS,6aR,8aR,12aS,14R,14aS,14bR)-14-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:	Sandorinic acid C
Standard InCHIKey:	ARUDPAROWGJVLG-FUPYXVGYSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)20-9-8-18-19(28(20,5)11-10-22(25)31)16-23(32)30(7)21-17-27(4,24(33)34)13-12-26(21,3)14-15-29(18,30)6/h20-21,23,32H,8-17H2,1-7H3,(H,33,34)/t20-,21+,23+,26+,27+,28+,29+,30+/m0/s1
SMILES:	OC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)[C@H](O)CC3=C([C@]1(CC2)C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465067
PubChem CID:	11048975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO26165	Sandoricum indicum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575968]
NPO26165	Sandoricum indicum	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2831	Cell Line	P388/S	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[474398]
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[474398]

☑ 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 NPC56588 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	216
0.1-0.2	1464
0.2-0.3	5866
0.3-0.4	15400
0.4-0.5	7402
0.5-0.6	5887
0.6-0.7	4524
0.7-0.8	1563
0.8-0.85	265
0.85-0.9	106
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC171789
0.9412	High Similarity	NPC235704
0.9176	High Similarity	NPC274330
0.9176	High Similarity	NPC143232
0.9176	High Similarity	NPC198664
0.9167	High Similarity	NPC71507
0.908	High Similarity	NPC133579
0.908	High Similarity	NPC474806
0.907	High Similarity	NPC111110
0.907	High Similarity	NPC291028
0.907	High Similarity	NPC470589
0.907	High Similarity	NPC46441
0.907	High Similarity	NPC126369
0.9059	High Similarity	NPC470629
0.9059	High Similarity	NPC474512
0.9059	High Similarity	NPC17733
0.9059	High Similarity	NPC52169
0.9059	High Similarity	NPC290690
0.9059	High Similarity	NPC182797
0.9059	High Similarity	NPC181225
0.9059	High Similarity	NPC473242
0.9048	High Similarity	NPC72638
0.8977	High Similarity	NPC80365
0.8966	High Similarity	NPC65120
0.8966	High Similarity	NPC105189
0.8966	High Similarity	NPC4036
0.8966	High Similarity	NPC145067
0.8966	High Similarity	NPC474525
0.8966	High Similarity	NPC158030
0.8966	High Similarity	NPC187722
0.8966	High Similarity	NPC38754
0.8966	High Similarity	NPC233455
0.8966	High Similarity	NPC301244
0.8953	High Similarity	NPC290972
0.8953	High Similarity	NPC234346
0.8953	High Similarity	NPC263393
0.8953	High Similarity	NPC127689
0.8953	High Similarity	NPC61543
0.8953	High Similarity	NPC64872
0.8953	High Similarity	NPC470588
0.8953	High Similarity	NPC270768
0.8953	High Similarity	NPC121798
0.8953	High Similarity	NPC59263
0.8953	High Similarity	NPC293048
0.8953	High Similarity	NPC225585
0.8953	High Similarity	NPC25906
0.8953	High Similarity	NPC474686
0.8953	High Similarity	NPC130520
0.8941	High Similarity	NPC293564
0.8941	High Similarity	NPC307426
0.8941	High Similarity	NPC130577
0.8941	High Similarity	NPC242468
0.8941	High Similarity	NPC102683
0.8941	High Similarity	NPC171203
0.8941	High Similarity	NPC68160
0.8941	High Similarity	NPC142415
0.8941	High Similarity	NPC18064
0.8941	High Similarity	NPC88716
0.8941	High Similarity	NPC98442
0.8941	High Similarity	NPC51700
0.8876	High Similarity	NPC32118
0.8864	High Similarity	NPC229281
0.8864	High Similarity	NPC118519
0.8864	High Similarity	NPC202728
0.8864	High Similarity	NPC272075
0.8864	High Similarity	NPC295643
0.8864	High Similarity	NPC214756
0.8864	High Similarity	NPC158059
0.8851	High Similarity	NPC474728
0.8851	High Similarity	NPC49320
0.8851	High Similarity	NPC290614
0.8851	High Similarity	NPC18872
0.8851	High Similarity	NPC130278
0.8851	High Similarity	NPC210037
0.8851	High Similarity	NPC120968
0.8851	High Similarity	NPC273621
0.8851	High Similarity	NPC193750
0.8851	High Similarity	NPC227467
0.8851	High Similarity	NPC477872
0.8851	High Similarity	NPC7260
0.8837	High Similarity	NPC246708
0.8837	High Similarity	NPC230387
0.8837	High Similarity	NPC1753
0.8837	High Similarity	NPC474511
0.8837	High Similarity	NPC40552
0.881	High Similarity	NPC180834
0.8795	High Similarity	NPC73882
0.8778	High Similarity	NPC88847
0.8778	High Similarity	NPC62516
0.8778	High Similarity	NPC157113
0.8764	High Similarity	NPC474529
0.8764	High Similarity	NPC209868
0.8764	High Similarity	NPC159365
0.8764	High Similarity	NPC87095
0.8764	High Similarity	NPC6818
0.8764	High Similarity	NPC191412
0.8764	High Similarity	NPC114159
0.875	High Similarity	NPC324341
0.875	High Similarity	NPC52021
0.875	High Similarity	NPC282616
0.875	High Similarity	NPC470590
0.875	High Similarity	NPC285184
0.875	High Similarity	NPC6255
0.875	High Similarity	NPC235884
0.875	High Similarity	NPC472149
0.875	High Similarity	NPC84319
0.875	High Similarity	NPC966
0.875	High Similarity	NPC471588
0.875	High Similarity	NPC71074
0.875	High Similarity	NPC60755
0.875	High Similarity	NPC475708
0.875	High Similarity	NPC25299
0.875	High Similarity	NPC228784
0.875	High Similarity	NPC288833
0.875	High Similarity	NPC300351
0.875	High Similarity	NPC306541
0.875	High Similarity	NPC77099
0.875	High Similarity	NPC155120
0.8736	High Similarity	NPC95246
0.8736	High Similarity	NPC281524
0.8736	High Similarity	NPC474972
0.8736	High Similarity	NPC161751
0.8736	High Similarity	NPC30522
0.8721	High Similarity	NPC173089
0.8721	High Similarity	NPC158141
0.8721	High Similarity	NPC73064
0.8706	High Similarity	NPC133954
0.8681	High Similarity	NPC21728
0.8667	High Similarity	NPC148523
0.8667	High Similarity	NPC473240
0.8667	High Similarity	NPC139570
0.8667	High Similarity	NPC96916
0.8652	High Similarity	NPC307335
0.8652	High Similarity	NPC118490
0.8652	High Similarity	NPC74855
0.8652	High Similarity	NPC298554
0.8652	High Similarity	NPC275809
0.8652	High Similarity	NPC136313
0.8652	High Similarity	NPC86368
0.8636	High Similarity	NPC86372
0.8636	High Similarity	NPC172361
0.8636	High Similarity	NPC113989
0.8636	High Similarity	NPC120840
0.8621	High Similarity	NPC242864
0.8621	High Similarity	NPC474474
0.8605	High Similarity	NPC475862
0.8605	High Similarity	NPC74363
0.8605	High Similarity	NPC73038
0.8605	High Similarity	NPC213412
0.8571	High Similarity	NPC69101
0.8571	High Similarity	NPC73004
0.8571	High Similarity	NPC476318
0.8571	High Similarity	NPC251779
0.8571	High Similarity	NPC173744
0.8571	High Similarity	NPC207922
0.8571	High Similarity	NPC310989
0.8571	High Similarity	NPC9487
0.8571	High Similarity	NPC327179
0.8571	High Similarity	NPC98874
0.8571	High Similarity	NPC259733
0.8571	High Similarity	NPC132824
0.8571	High Similarity	NPC476327
0.8571	High Similarity	NPC158371
0.8571	High Similarity	NPC116457
0.8571	High Similarity	NPC204961
0.8556	High Similarity	NPC91010
0.8556	High Similarity	NPC282395
0.8556	High Similarity	NPC263548
0.8556	High Similarity	NPC231063
0.8556	High Similarity	NPC145667
0.8556	High Similarity	NPC299996
0.8556	High Similarity	NPC32407
0.8556	High Similarity	NPC23170
0.8556	High Similarity	NPC222047
0.8556	High Similarity	NPC20235
0.8556	High Similarity	NPC88116
0.8556	High Similarity	NPC148964
0.8556	High Similarity	NPC74751
0.8523	High Similarity	NPC477973
0.8523	High Similarity	NPC474700
0.8506	High Similarity	NPC477926
0.8478	Intermediate Similarity	NPC9613
0.8478	Intermediate Similarity	NPC43686
0.8478	Intermediate Similarity	NPC187933
0.8478	Intermediate Similarity	NPC247139
0.8478	Intermediate Similarity	NPC189880
0.8478	Intermediate Similarity	NPC255589
0.8478	Intermediate Similarity	NPC259788
0.8462	Intermediate Similarity	NPC474727
0.8462	Intermediate Similarity	NPC195715
0.8462	Intermediate Similarity	NPC198245
0.8452	Intermediate Similarity	NPC3915
0.8452	Intermediate Similarity	NPC263272
0.8452	Intermediate Similarity	NPC473420
0.8452	Intermediate Similarity	NPC162632
0.8452	Intermediate Similarity	NPC267691
0.8452	Intermediate Similarity	NPC274050
0.8444	Intermediate Similarity	NPC49776
0.8444	Intermediate Similarity	NPC474436
0.8444	Intermediate Similarity	NPC211230

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 NPC56588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1911
0.2-0.3	3874
0.3-0.4	2163
0.4-0.5	567
0.5-0.6	205
0.6-0.7	180
0.7-0.8	55
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD7515	Phase 2
0.8556	High Similarity	NPD7748	Approved
0.8315	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7902	Approved
0.8161	Intermediate Similarity	NPD4786	Approved
0.814	Intermediate Similarity	NPD3667	Approved
0.8068	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.7957	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7900	Approved
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7717	Intermediate Similarity	NPD5328	Approved
0.7647	Intermediate Similarity	NPD6117	Approved
0.7647	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7614	Phase 1
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7558	Intermediate Similarity	NPD6116	Phase 1
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD6411	Approved
0.7553	Intermediate Similarity	NPD6079	Approved
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7471	Intermediate Similarity	NPD6697	Approved
0.7471	Intermediate Similarity	NPD6115	Approved
0.7471	Intermediate Similarity	NPD6118	Approved
0.7471	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6684	Approved
0.7391	Intermediate Similarity	NPD5330	Approved
0.7391	Intermediate Similarity	NPD6409	Approved
0.7391	Intermediate Similarity	NPD7146	Approved
0.7391	Intermediate Similarity	NPD7334	Approved
0.7391	Intermediate Similarity	NPD7521	Approved
0.7381	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD6101	Approved
0.734	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4695	Discontinued
0.7292	Intermediate Similarity	NPD4202	Approved
0.7273	Intermediate Similarity	NPD3617	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7245	Intermediate Similarity	NPD5222	Approved
0.7245	Intermediate Similarity	NPD4697	Phase 3
0.7245	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD7732	Phase 3
0.7245	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5737	Approved
0.7234	Intermediate Similarity	NPD6903	Approved
0.7234	Intermediate Similarity	NPD6672	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD4755	Approved
0.7172	Intermediate Similarity	NPD5173	Approved
0.7158	Intermediate Similarity	NPD4753	Phase 2
0.7156	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD3573	Approved
0.7126	Intermediate Similarity	NPD7339	Approved
0.7126	Intermediate Similarity	NPD6942	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7111	Intermediate Similarity	NPD7525	Registered
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7065	Intermediate Similarity	NPD4788	Approved
0.7059	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD4245	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7048	Intermediate Similarity	NPD6011	Approved
0.7045	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4139	Approved
0.7033	Intermediate Similarity	NPD4692	Approved
0.703	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD4696	Approved
0.703	Intermediate Similarity	NPD5285	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.7021	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5284	Approved
0.701	Intermediate Similarity	NPD5281	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.6988	Remote Similarity	NPD4224	Phase 2
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6977	Remote Similarity	NPD6081	Approved
0.6961	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD4221	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6941	Remote Similarity	NPD3698	Phase 2
0.6939	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD5778	Approved
0.6932	Remote Similarity	NPD3703	Phase 2
0.6931	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD4748	Discontinued
0.6923	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5329	Approved
0.6893	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD4633	Approved
0.6893	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD5225	Approved
0.6893	Remote Similarity	NPD5224	Approved
0.686	Remote Similarity	NPD4789	Approved
0.6842	Remote Similarity	NPD6098	Approved
0.6827	Remote Similarity	NPD4754	Approved
0.6827	Remote Similarity	NPD5174	Approved
0.6827	Remote Similarity	NPD5175	Approved
0.6824	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5360	Phase 3
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4197	Approved
0.6804	Remote Similarity	NPD6904	Approved
0.6804	Remote Similarity	NPD6080	Approved
0.6804	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD5210	Approved
0.68	Remote Similarity	NPD4629	Approved
0.68	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6412	Phase 2
0.6783	Remote Similarity	NPD8328	Phase 3
0.6782	Remote Similarity	NPD5777	Approved
0.6762	Remote Similarity	NPD5141	Approved
0.6757	Remote Similarity	NPD6868	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6703	Remote Similarity	NPD3671	Phase 1
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6637	Remote Similarity	NPD6335	Approved
0.6607	Remote Similarity	NPD6274	Approved
0.6606	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4225	Approved
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD5168	Approved
0.6574	Remote Similarity	NPD5128	Approved
0.6574	Remote Similarity	NPD4730	Approved
0.6574	Remote Similarity	NPD4729	Approved
0.6566	Remote Similarity	NPD5692	Phase 3
0.6562	Remote Similarity	NPD1694	Approved
0.6556	Remote Similarity	NPD8264	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6549	Remote Similarity	NPD6009	Approved
0.6531	Remote Similarity	NPD5208	Approved
0.65	Remote Similarity	NPD5694	Approved
0.65	Remote Similarity	NPD5693	Phase 1
0.6491	Remote Similarity	NPD6313	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6489	Remote Similarity	NPD8028	Phase 2
0.6489	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD7341	Phase 2
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6455	Remote Similarity	NPD5248	Approved
0.6455	Remote Similarity	NPD5247	Approved
0.6455	Remote Similarity	NPD5135	Approved
0.6455	Remote Similarity	NPD5249	Phase 3
0.6455	Remote Similarity	NPD5250	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