NPASS Compound

Structure

NPC471599 OpenBabel07101719512D 38 39 0 0 1 0 0 0 0 0999 V2000 7.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5946 -4.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7536 -3.6036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 5.7709 -2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2709 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -3.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8025 -3.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 -1.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2673 -2.2653 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 4.7709 -0.3660 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 -1.5962 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 4.2709 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2183 -1.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.5000 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 8 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 18 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 10 17 2 0 0 0 0 10 24 1 0 0 0 0 11 18 1 0 0 0 0 11 25 1 0 0 0 0 12 21 2 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 34 1 0 0 0 0 14 20 2 0 0 0 0 14 35 1 0 0 0 0 15 28 1 0 0 0 0 15 36 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 6 0 0 0 22 37 1 0 0 0 0 23 30 2 0 0 0 0 23 36 1 0 0 0 0 24 31 2 0 0 0 0 24 38 1 0 0 0 0 25 32 2 0 0 0 0 25 37 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 1 0 0 0 27 35 1 0 0 0 0 27 38 1 6 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.26
Volume:	545.178
LogP:	4.197
LogD:	2.746
LogS:	-4.552
# Rotatable Bonds:	16
TPSA:	134.66
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	4.953
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.604
MDCK Permeability:	4.0450249798595905e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	74.59496307373047%
Volume Distribution (VD):	1.394
Pgp-substrate:	15.546936988830566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	5.608
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.216
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.421
AMES Toxicity:	0.988
Rat Oral Acute Toxicity:	0.664
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.967
Carcinogencity:	0.908
Eye Corrosion:	0.013
Eye Irritation:	0.049
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC471599

Natural Product ID:	NPC471599
*Common Name:**	[(1S,6S,7R,7As)-4-(Acetyloxymethyl)-7-Hydroxy-7-(3-Methylbutanoyloxymethyl)-1-(3-Methylbut-2-Enoyloxy)-6,7A-Dihydro-1H-Cyclopenta[C]Pyran-6-Yl] 3-Methylpentanoate
IUPAC Name:	[(1S,6S,7R,7aS)-4-(acetyloxymethyl)-7-hydroxy-7-(3-methylbutanoyloxymethyl)-1-(3-methylbut-2-enoyloxy)-6,7a-dihydro-1H-cyclopenta[c]pyran-6-yl] 3-methylpentanoate
Synonyms:
Standard InCHIKey:	YDYHOAALGZGNKR-KTIJEDIRSA-N
Standard InCHI:	InChI=1S/C28H40O10/c1-8-18(6)11-25(32)37-22-12-21-20(13-34-19(7)29)14-35-27(38-24(31)10-17(4)5)26(21)28(22,33)15-36-23(30)9-16(2)3/h10,12,14,16,18,22,26-27,33H,8-9,11,13,15H2,1-7H3/t18?,22-,26+,27-,28+/m0/s1
SMILES:	CCC(CC(=O)O[C@H]1C=C2[C@@H]([C@@]1(O)COC(=O)CC(C)C)[C@@H](OC=C2COC(=O)C)OC(=O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL273967
PubChem CID:	24763334
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids 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
NPO33249	valeriana sorbifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18052324]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7300.0	nM	PMID[552023]

☑ 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 NPC471599 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	209
0.1-0.2	1235
0.2-0.3	4358
0.3-0.4	8212
0.4-0.5	15935
0.5-0.6	8603
0.6-0.7	3673
0.7-0.8	433
0.8-0.85	25
0.85-0.9	3
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC219038
0.9681	High Similarity	NPC151093
0.9579	High Similarity	NPC244878
0.9479	High Similarity	NPC4637
0.9479	High Similarity	NPC98859
0.9479	High Similarity	NPC20673
0.9271	High Similarity	NPC473307
0.9271	High Similarity	NPC124181
0.9167	High Similarity	NPC153559
0.8958	High Similarity	NPC291709
0.8958	High Similarity	NPC241407
0.8878	High Similarity	NPC90819
0.8447	Intermediate Similarity	NPC86095
0.8431	Intermediate Similarity	NPC222062
0.8416	Intermediate Similarity	NPC22149
0.8416	Intermediate Similarity	NPC306344
0.8416	Intermediate Similarity	NPC255677
0.835	Intermediate Similarity	NPC118761
0.835	Intermediate Similarity	NPC284929
0.835	Intermediate Similarity	NPC267869
0.835	Intermediate Similarity	NPC234304
0.835	Intermediate Similarity	NPC197541
0.8333	Intermediate Similarity	NPC298255
0.8333	Intermediate Similarity	NPC28304
0.8283	Intermediate Similarity	NPC274588
0.8252	Intermediate Similarity	NPC13171
0.8252	Intermediate Similarity	NPC310804
0.8252	Intermediate Similarity	NPC195510
0.8252	Intermediate Similarity	NPC261117
0.82	Intermediate Similarity	NPC6765
0.82	Intermediate Similarity	NPC93869
0.8119	Intermediate Similarity	NPC170527
0.8119	Intermediate Similarity	NPC241911
0.8077	Intermediate Similarity	NPC250545
0.8	Intermediate Similarity	NPC61201
0.8	Intermediate Similarity	NPC320552
0.798	Intermediate Similarity	NPC327253
0.7965	Intermediate Similarity	NPC219656
0.7944	Intermediate Similarity	NPC474285
0.7944	Intermediate Similarity	NPC254538
0.7885	Intermediate Similarity	NPC476320
0.7885	Intermediate Similarity	NPC476211
0.7864	Intermediate Similarity	NPC86843
0.7843	Intermediate Similarity	NPC170204
0.783	Intermediate Similarity	NPC475928
0.783	Intermediate Similarity	NPC37240
0.7826	Intermediate Similarity	NPC233500
0.7822	Intermediate Similarity	NPC472196
0.7822	Intermediate Similarity	NPC472195
0.7822	Intermediate Similarity	NPC238090
0.7822	Intermediate Similarity	NPC280390
0.781	Intermediate Similarity	NPC476230
0.781	Intermediate Similarity	NPC27474
0.781	Intermediate Similarity	NPC216911
0.78	Intermediate Similarity	NPC303451
0.78	Intermediate Similarity	NPC6414
0.7788	Intermediate Similarity	NPC472015
0.7778	Intermediate Similarity	NPC148270
0.7778	Intermediate Similarity	NPC197813
0.7778	Intermediate Similarity	NPC80338
0.7768	Intermediate Similarity	NPC106446
0.7767	Intermediate Similarity	NPC284063
0.7767	Intermediate Similarity	NPC54731
0.7767	Intermediate Similarity	NPC306041
0.7759	Intermediate Similarity	NPC196130
0.7745	Intermediate Similarity	NPC159698
0.7745	Intermediate Similarity	NPC256368
0.7736	Intermediate Similarity	NPC177013
0.7736	Intermediate Similarity	NPC4899
0.7736	Intermediate Similarity	NPC474730
0.7736	Intermediate Similarity	NPC35185
0.7723	Intermediate Similarity	NPC66504
0.7723	Intermediate Similarity	NPC477749
0.7719	Intermediate Similarity	NPC13710
0.7714	Intermediate Similarity	NPC473146
0.7714	Intermediate Similarity	NPC130792
0.77	Intermediate Similarity	NPC477748
0.7692	Intermediate Similarity	NPC472290
0.7692	Intermediate Similarity	NPC471490
0.7692	Intermediate Similarity	NPC219804
0.7685	Intermediate Similarity	NPC170432
0.7672	Intermediate Similarity	NPC470829
0.7672	Intermediate Similarity	NPC473228
0.767	Intermediate Similarity	NPC471492
0.767	Intermediate Similarity	NPC469543
0.7664	Intermediate Similarity	NPC329834
0.7664	Intermediate Similarity	NPC329704
0.7664	Intermediate Similarity	NPC197736
0.7647	Intermediate Similarity	NPC320089
0.7642	Intermediate Similarity	NPC476228
0.7624	Intermediate Similarity	NPC202886
0.7624	Intermediate Similarity	NPC117596
0.7624	Intermediate Similarity	NPC474098
0.7624	Intermediate Similarity	NPC475995
0.7624	Intermediate Similarity	NPC118078
0.7619	Intermediate Similarity	NPC203627
0.76	Intermediate Similarity	NPC233997
0.7596	Intermediate Similarity	NPC288350
0.7596	Intermediate Similarity	NPC173329
0.7573	Intermediate Similarity	NPC472198
0.7573	Intermediate Similarity	NPC294293
0.757	Intermediate Similarity	NPC106668
0.7568	Intermediate Similarity	NPC193741
0.7551	Intermediate Similarity	NPC266718
0.7549	Intermediate Similarity	NPC472199
0.7549	Intermediate Similarity	NPC9447
0.7549	Intermediate Similarity	NPC472197
0.7549	Intermediate Similarity	NPC472125
0.7549	Intermediate Similarity	NPC472126
0.7549	Intermediate Similarity	NPC472124
0.7549	Intermediate Similarity	NPC235051
0.7545	Intermediate Similarity	NPC177524
0.7545	Intermediate Similarity	NPC110701
0.7545	Intermediate Similarity	NPC392
0.7545	Intermediate Similarity	NPC219900
0.7541	Intermediate Similarity	NPC155529
0.7525	Intermediate Similarity	NPC249408
0.7525	Intermediate Similarity	NPC104129
0.7525	Intermediate Similarity	NPC50464
0.7524	Intermediate Similarity	NPC2666
0.7523	Intermediate Similarity	NPC239961
0.7523	Intermediate Similarity	NPC82251
0.7523	Intermediate Similarity	NPC470980
0.7523	Intermediate Similarity	NPC127235
0.7522	Intermediate Similarity	NPC287075
0.75	Intermediate Similarity	NPC268326
0.75	Intermediate Similarity	NPC27687
0.75	Intermediate Similarity	NPC220221
0.75	Intermediate Similarity	NPC158350
0.75	Intermediate Similarity	NPC153085
0.75	Intermediate Similarity	NPC142583
0.75	Intermediate Similarity	NPC45409
0.7477	Intermediate Similarity	NPC133625
0.7477	Intermediate Similarity	NPC287539
0.7477	Intermediate Similarity	NPC198992
0.7477	Intermediate Similarity	NPC316974
0.7477	Intermediate Similarity	NPC3488
0.7476	Intermediate Similarity	NPC476300
0.7475	Intermediate Similarity	NPC470658
0.7455	Intermediate Similarity	NPC26617
0.7451	Intermediate Similarity	NPC473311
0.7451	Intermediate Similarity	NPC177668
0.7451	Intermediate Similarity	NPC307699
0.7449	Intermediate Similarity	NPC475714
0.7434	Intermediate Similarity	NPC475851
0.7434	Intermediate Similarity	NPC475924
0.7434	Intermediate Similarity	NPC241477
0.7431	Intermediate Similarity	NPC474917
0.7431	Intermediate Similarity	NPC307846
0.7431	Intermediate Similarity	NPC305157
0.7429	Intermediate Similarity	NPC161293
0.7429	Intermediate Similarity	NPC473333
0.7426	Intermediate Similarity	NPC473658
0.7417	Intermediate Similarity	NPC179261
0.7414	Intermediate Similarity	NPC473617
0.7414	Intermediate Similarity	NPC473828
0.7411	Intermediate Similarity	NPC119550
0.7411	Intermediate Similarity	NPC15551
0.7407	Intermediate Similarity	NPC86077
0.7407	Intermediate Similarity	NPC470972
0.7407	Intermediate Similarity	NPC201191
0.7404	Intermediate Similarity	NPC477131
0.74	Intermediate Similarity	NPC186332
0.74	Intermediate Similarity	NPC208473
0.74	Intermediate Similarity	NPC471480
0.74	Intermediate Similarity	NPC47220
0.74	Intermediate Similarity	NPC311163
0.7391	Intermediate Similarity	NPC277583
0.7391	Intermediate Similarity	NPC207637
0.7387	Intermediate Similarity	NPC135015
0.7387	Intermediate Similarity	NPC217921
0.7387	Intermediate Similarity	NPC475960
0.7387	Intermediate Similarity	NPC128795
0.7387	Intermediate Similarity	NPC48548
0.7387	Intermediate Similarity	NPC311223
0.7387	Intermediate Similarity	NPC473807
0.7379	Intermediate Similarity	NPC473150
0.7379	Intermediate Similarity	NPC294643
0.7379	Intermediate Similarity	NPC274274
0.7374	Intermediate Similarity	NPC475035
0.7374	Intermediate Similarity	NPC475706
0.7374	Intermediate Similarity	NPC473308
0.7374	Intermediate Similarity	NPC136699
0.7374	Intermediate Similarity	NPC220167
0.7368	Intermediate Similarity	NPC101965
0.7368	Intermediate Similarity	NPC101400
0.7364	Intermediate Similarity	NPC223450
0.7364	Intermediate Similarity	NPC85670
0.7358	Intermediate Similarity	NPC476613
0.7358	Intermediate Similarity	NPC476612
0.7358	Intermediate Similarity	NPC236580
0.7358	Intermediate Similarity	NPC304445
0.7358	Intermediate Similarity	NPC474182
0.7353	Intermediate Similarity	NPC133450
0.7353	Intermediate Similarity	NPC307092
0.7353	Intermediate Similarity	NPC93190
0.7347	Intermediate Similarity	NPC251026
0.7345	Intermediate Similarity	NPC71680
0.7339	Intermediate Similarity	NPC473148
0.7333	Intermediate Similarity	NPC471141

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 NPC471599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1647
0.2-0.3	3639
0.3-0.4	2415
0.4-0.5	976
0.5-0.6	221
0.6-0.7	61
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7672	Intermediate Similarity	NPD7503	Approved
0.7545	Intermediate Similarity	NPD6686	Approved
0.7455	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6698	Approved
0.7451	Intermediate Similarity	NPD7838	Discovery
0.7451	Intermediate Similarity	NPD46	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7119	Intermediate Similarity	NPD7327	Approved
0.7119	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD6371	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.7083	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD7516	Approved
0.7043	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8294	Approved
0.7	Intermediate Similarity	NPD8377	Approved
0.699	Remote Similarity	NPD4250	Approved
0.699	Remote Similarity	NPD4251	Approved
0.696	Remote Similarity	NPD7319	Approved
0.6942	Remote Similarity	NPD8379	Approved
0.6942	Remote Similarity	NPD8378	Approved
0.6942	Remote Similarity	NPD8296	Approved
0.6942	Remote Similarity	NPD8515	Approved
0.6942	Remote Similarity	NPD8335	Approved
0.6942	Remote Similarity	NPD8516	Approved
0.6942	Remote Similarity	NPD8517	Approved
0.6942	Remote Similarity	NPD8380	Approved
0.6893	Remote Similarity	NPD4249	Approved
0.6887	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD6412	Phase 2
0.6765	Remote Similarity	NPD7154	Phase 3
0.6757	Remote Similarity	NPD6648	Approved
0.6698	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD7638	Approved
0.6639	Remote Similarity	NPD8133	Approved
0.6634	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7640	Approved
0.6607	Remote Similarity	NPD7639	Approved
0.656	Remote Similarity	NPD7829	Approved
0.656	Remote Similarity	NPD7830	Approved
0.6538	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD4822	Approved
0.6457	Remote Similarity	NPD8451	Approved
0.6455	Remote Similarity	NPD5282	Discontinued
0.6442	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD6110	Phase 1
0.6436	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD4268	Approved
0.6423	Remote Similarity	NPD7641	Discontinued
0.6422	Remote Similarity	NPD7637	Suspended
0.6406	Remote Similarity	NPD8448	Approved
0.6406	Remote Similarity	NPD8074	Phase 3
0.64	Remote Similarity	NPD8444	Approved
0.6372	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6355	Remote Similarity	NPD7524	Approved
0.6341	Remote Similarity	NPD7115	Discovery
0.6339	Remote Similarity	NPD7839	Suspended
0.6299	Remote Similarity	NPD7642	Approved
0.6279	Remote Similarity	NPD8293	Discontinued
0.626	Remote Similarity	NPD8390	Approved
0.626	Remote Similarity	NPD8392	Approved
0.626	Remote Similarity	NPD8391	Approved
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD8340	Approved
0.6231	Remote Similarity	NPD7736	Approved
0.6226	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8080	Discontinued
0.622	Remote Similarity	NPD6370	Approved
0.621	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5209	Approved
0.6182	Remote Similarity	NPD5785	Approved
0.6168	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6882	Approved
0.6132	Remote Similarity	NPD6695	Phase 3
0.6132	Remote Similarity	NPD5331	Approved
0.6132	Remote Similarity	NPD5332	Approved
0.6124	Remote Similarity	NPD7492	Approved
0.6116	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4790	Discontinued
0.609	Remote Similarity	NPD7260	Phase 2
0.608	Remote Similarity	NPD6009	Approved
0.6077	Remote Similarity	NPD6616	Approved
0.6068	Remote Similarity	NPD7632	Discontinued
0.6063	Remote Similarity	NPD6054	Approved
0.6063	Remote Similarity	NPD6319	Approved
0.6063	Remote Similarity	NPD6059	Approved
0.6047	Remote Similarity	NPD8328	Phase 3
0.6038	Remote Similarity	NPD6435	Approved
0.6033	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7078	Approved
0.6019	Remote Similarity	NPD5363	Approved
0.6016	Remote Similarity	NPD8297	Approved
0.6016	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.5985	Remote Similarity	NPD8337	Approved
0.5985	Remote Similarity	NPD8336	Approved
0.5968	Remote Similarity	NPD4632	Approved
0.5965	Remote Similarity	NPD5695	Phase 3
0.5954	Remote Similarity	NPD8273	Phase 1
0.5952	Remote Similarity	NPD7500	Approved
0.5946	Remote Similarity	NPD6101	Approved
0.5946	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5369	Approved
0.5929	Remote Similarity	NPD6399	Phase 3
0.5917	Remote Similarity	NPD6402	Approved
0.5917	Remote Similarity	NPD6675	Approved
0.5917	Remote Similarity	NPD5739	Approved
0.5917	Remote Similarity	NPD7128	Approved
0.5913	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7750	Discontinued
0.5902	Remote Similarity	NPD6372	Approved
0.5902	Remote Similarity	NPD6373	Approved
0.5891	Remote Similarity	NPD6016	Approved
0.5891	Remote Similarity	NPD6015	Approved
0.5888	Remote Similarity	NPD4269	Approved
0.5888	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4270	Approved
0.5887	Remote Similarity	NPD969	Suspended
0.5868	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6685	Approved
0.5865	Remote Similarity	NPD4756	Discovery
0.5849	Remote Similarity	NPD6931	Approved
0.5849	Remote Similarity	NPD6930	Phase 2
0.5849	Remote Similarity	NPD4252	Approved
0.5849	Remote Similarity	NPD7332	Phase 2
0.5849	Remote Similarity	NPD5368	Approved
0.5846	Remote Similarity	NPD5988	Approved
0.5841	Remote Similarity	NPD5281	Approved
0.5841	Remote Similarity	NPD5284	Approved
0.5841	Remote Similarity	NPD6411	Approved
0.5827	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7505	Discontinued
0.582	Remote Similarity	NPD7320	Approved
0.582	Remote Similarity	NPD6881	Approved
0.582	Remote Similarity	NPD6899	Approved
0.5818	Remote Similarity	NPD5786	Approved
0.5812	Remote Similarity	NPD5696	Approved
0.581	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD8338	Approved
0.5809	Remote Similarity	NPD6845	Suspended
0.5806	Remote Similarity	NPD6649	Approved
0.5806	Remote Similarity	NPD6650	Approved
0.5806	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6051	Approved
0.5802	Remote Similarity	NPD6067	Discontinued
0.5785	Remote Similarity	NPD6008	Approved
0.5785	Remote Similarity	NPD6640	Phase 3
0.5769	Remote Similarity	NPD6933	Approved
0.5755	Remote Similarity	NPD6929	Approved
0.575	Remote Similarity	NPD6647	Phase 2
0.5741	Remote Similarity	NPD7685	Pre-registration
0.5738	Remote Similarity	NPD5697	Approved
0.5738	Remote Similarity	NPD5701	Approved
0.5726	Remote Similarity	NPD7102	Approved
0.5726	Remote Similarity	NPD7290	Approved
0.5726	Remote Similarity	NPD6883	Approved
0.5726	Remote Similarity	NPD6421	Discontinued
0.5724	Remote Similarity	NPD7625	Phase 1
0.5714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6050	Approved
0.5702	Remote Similarity	NPD5693	Phase 1
0.5702	Remote Similarity	NPD7087	Discontinued
0.5701	Remote Similarity	NPD7514	Phase 3
0.5692	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7604	Phase 2
0.568	Remote Similarity	NPD6869	Approved
0.568	Remote Similarity	NPD8130	Phase 1
0.568	Remote Similarity	NPD6617	Approved
0.568	Remote Similarity	NPD6847	Approved
0.568	Remote Similarity	NPD2204	Approved
0.5676	Remote Similarity	NPD7521	Approved
0.5676	Remote Similarity	NPD7334	Approved
0.5676	Remote Similarity	NPD6409	Approved
0.5676	Remote Similarity	NPD6684	Approved
0.5676	Remote Similarity	NPD7146	Approved
0.5676	Remote Similarity	NPD5330	Approved
0.5673	Remote Similarity	NPD8039	Approved
0.5649	Remote Similarity	NPD5983	Phase 2
0.5648	Remote Similarity	NPD6898	Phase 1
0.5645	Remote Similarity	NPD6013	Approved
0.5645	Remote Similarity	NPD6014	Approved
0.5645	Remote Similarity	NPD6012	Approved
0.5635	Remote Similarity	NPD6912	Phase 3
0.563	Remote Similarity	NPD6033	Approved
0.5625	Remote Similarity	NPD7266	Discontinued

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