NPASS Compound

Structure

NPC471974 OpenBabel07101719252D 44 47 0 0 1 0 0 0 0 0999 V2000 -2.5957 -1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4050 -2.7468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9710 -0.4162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2113 1.2991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2920 2.8018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6369 2.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9782 -4.0839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7526 -4.1486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5553 1.5999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3456 1.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6741 -2.6821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8274 -2.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2685 0.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1422 0.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6056 0.6495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9903 -0.1387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9065 1.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1111 -1.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9034 -2.0853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5713 -0.1304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5583 -2.2148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5960 0.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6118 2.0688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0941 -3.6166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2530 -0.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0567 -2.6173 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2264 0.3801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2514 0.6027 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0003 0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9848 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3793 -1.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8410 -1.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4267 0.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4806 0.6027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.0860 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 2.5211 -0.5754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8740 0.8571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8430 -1.1427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3637 -2.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6103 -1.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1357 -2.2641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6492 1.4150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 24 2 0 0 0 0 8 24 1 0 0 0 0 9 35 1 0 0 0 0 10 35 1 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 30 1 0 0 0 0 19 26 1 0 0 0 0 20 36 1 0 0 0 0 24 26 1 0 0 0 0 25 31 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 1 0 0 0 28 20 1 1 0 0 0 28 35 1 0 0 0 0 29 30 2 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 41 2 0 0 0 0 32 36 1 0 0 0 0 32 37 1 0 0 0 0 32 42 2 0 0 0 0 33 36 1 0 0 0 0 33 38 1 0 0 0 0 33 43 2 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 35 37 1 0 0 0 0 36 19 1 1 0 0 0 37 16 1 6 0 0 0 38 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.35
Volume:	655.318
LogP:	8.032
LogD:	5.577
LogS:	-4.818
# Rotatable Bonds:	10
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	6.346
Fsp3:	0.526
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.076
MDCK Permeability:	1.3601562386611477e-05
Pgp-inhibitor:	0.078
Pgp-substrate:	0.512
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.734

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	95.88976287841797%
Volume Distribution (VD):	2.094
Pgp-substrate:	6.44536828994751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.538
CYP2C19-inhibitor:	0.783
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.513
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.74
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	14.731
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.789
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.231
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.02
Carcinogencity:	0.797
Eye Corrosion:	0.019
Eye Irritation:	0.282
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC471974

Natural Product ID:	NPC471974
*Common Name:**	PZEUWVRPGGVSMR-UJFGPWOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PZEUWVRPGGVSMR-UJFGPWOYSA-N
Standard InCHI:	InChI=1S/C38H48O6/c1-21(2)11-12-26(24(7)8)19-36-20-28-27(17-23(5)6)38(33(36)43,31(41)25-13-14-29(39)30(40)18-25)34(44)37(32(36)42,35(28,9)10)16-15-22(3)4/h11,13-15,17-18,26-28,39-40H,7,12,16,19-20H2,1-6,8-10H3/t26?,27-,28+,36+,37-,38-/m1/s1
SMILES:	CC(=CC[C@@]12C(=O)[C@]3(CC(C(=C)C)CC=C(C)C)C[C@H](C2(C)C)[C@H]([C@](C1=O)(C3=O)C(=O)c1ccc(c(c1)O)O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314601
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[24960143]

☑ 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	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[541682]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[541682]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	9100.0	nM	PMID[541682]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[541682]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[541682]

☑ 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 NPC471974 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	414
0.1-0.2	1590
0.2-0.3	3140
0.3-0.4	8038
0.4-0.5	10664
0.5-0.6	8819
0.6-0.7	9095
0.7-0.8	787
0.8-0.85	90
0.85-0.9	36
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469680
1.0	High Similarity	NPC469681
0.9552	High Similarity	NPC51531
0.9552	High Similarity	NPC289358
0.9552	High Similarity	NPC28592
0.9552	High Similarity	NPC5014
0.9552	High Similarity	NPC114333
0.9552	High Similarity	NPC473779
0.9552	High Similarity	NPC245760
0.9552	High Similarity	NPC50615
0.9552	High Similarity	NPC149773
0.9552	High Similarity	NPC469857
0.9552	High Similarity	NPC91887
0.9552	High Similarity	NPC473479
0.9552	High Similarity	NPC477849
0.9552	High Similarity	NPC23667
0.9552	High Similarity	NPC46242
0.9552	High Similarity	NPC165191
0.9552	High Similarity	NPC157284
0.9552	High Similarity	NPC297797
0.9552	High Similarity	NPC42384
0.9481	High Similarity	NPC294330
0.9412	High Similarity	NPC473527
0.9403	High Similarity	NPC7464
0.9281	High Similarity	NPC8493
0.9281	High Similarity	NPC294679
0.9281	High Similarity	NPC144247
0.9281	High Similarity	NPC145301
0.9281	High Similarity	NPC469375
0.9275	High Similarity	NPC471972
0.9275	High Similarity	NPC469855
0.9275	High Similarity	NPC471971
0.9275	High Similarity	NPC30846
0.9143	High Similarity	NPC469856
0.9143	High Similarity	NPC469854
0.9051	High Similarity	NPC277559
0.9051	High Similarity	NPC49911
0.9021	High Similarity	NPC46549
0.9021	High Similarity	NPC264229
0.9014	High Similarity	NPC471970
0.8993	High Similarity	NPC470035
0.8905	High Similarity	NPC43353
0.8897	High Similarity	NPC111845
0.8889	High Similarity	NPC132810
0.8881	High Similarity	NPC25736
0.8828	High Similarity	NPC237441
0.8806	High Similarity	NPC234175
0.8768	High Similarity	NPC153088
0.8759	High Similarity	NPC4170
0.8759	High Similarity	NPC138472
0.875	High Similarity	NPC273798
0.8732	High Similarity	NPC184935
0.8716	High Similarity	NPC305710
0.8681	High Similarity	NPC470038
0.8639	High Similarity	NPC48949
0.8623	High Similarity	NPC474715
0.8592	High Similarity	NPC476534
0.8592	High Similarity	NPC471853
0.8582	High Similarity	NPC230811
0.8511	High Similarity	NPC471152
0.8511	High Similarity	NPC118366
0.8489	Intermediate Similarity	NPC294226
0.8472	Intermediate Similarity	NPC169214
0.8472	Intermediate Similarity	NPC229218
0.8472	Intermediate Similarity	NPC192597
0.8472	Intermediate Similarity	NPC141817
0.8472	Intermediate Similarity	NPC248068
0.8472	Intermediate Similarity	NPC176030
0.8456	Intermediate Similarity	NPC176130
0.8456	Intermediate Similarity	NPC78364
0.8456	Intermediate Similarity	NPC69424
0.8456	Intermediate Similarity	NPC84672
0.8435	Intermediate Similarity	NPC52692
0.8435	Intermediate Similarity	NPC10842
0.8425	Intermediate Similarity	NPC75295
0.8414	Intermediate Similarity	NPC199936
0.8406	Intermediate Similarity	NPC108129
0.8389	Intermediate Similarity	NPC470037
0.838	Intermediate Similarity	NPC475957
0.837	Intermediate Similarity	NPC15127
0.8369	Intermediate Similarity	NPC258502
0.8358	Intermediate Similarity	NPC91478
0.8357	Intermediate Similarity	NPC477139
0.8355	Intermediate Similarity	NPC471968
0.8345	Intermediate Similarity	NPC469447
0.8345	Intermediate Similarity	NPC477873
0.8333	Intermediate Similarity	NPC276238
0.8322	Intermediate Similarity	NPC61398
0.8322	Intermediate Similarity	NPC416
0.8321	Intermediate Similarity	NPC72667
0.8321	Intermediate Similarity	NPC150919
0.8299	Intermediate Similarity	NPC258856
0.8298	Intermediate Similarity	NPC202225
0.8288	Intermediate Similarity	NPC224884
0.8288	Intermediate Similarity	NPC209085
0.8284	Intermediate Similarity	NPC120545
0.8273	Intermediate Similarity	NPC117609
0.8248	Intermediate Similarity	NPC254492
0.8248	Intermediate Similarity	NPC15837
0.8243	Intermediate Similarity	NPC143685
0.8239	Intermediate Similarity	NPC80035
0.8231	Intermediate Similarity	NPC53520
0.8231	Intermediate Similarity	NPC309169
0.8231	Intermediate Similarity	NPC196941
0.8214	Intermediate Similarity	NPC471851
0.8214	Intermediate Similarity	NPC291001
0.8214	Intermediate Similarity	NPC18798
0.8214	Intermediate Similarity	NPC243305
0.8212	Intermediate Similarity	NPC35
0.8201	Intermediate Similarity	NPC303910
0.8201	Intermediate Similarity	NPC171460
0.8194	Intermediate Similarity	NPC13715
0.8188	Intermediate Similarity	NPC324209
0.8176	Intermediate Similarity	NPC66894
0.8176	Intermediate Similarity	NPC8102
0.8169	Intermediate Similarity	NPC293454
0.8151	Intermediate Similarity	NPC472410
0.8129	Intermediate Similarity	NPC229894
0.8129	Intermediate Similarity	NPC96024
0.8125	Intermediate Similarity	NPC264022
0.8125	Intermediate Similarity	NPC147418
0.8112	Intermediate Similarity	NPC103082
0.8112	Intermediate Similarity	NPC72918
0.8112	Intermediate Similarity	NPC477596
0.8108	Intermediate Similarity	NPC79627
0.8106	Intermediate Similarity	NPC61062
0.8106	Intermediate Similarity	NPC277394
0.8106	Intermediate Similarity	NPC299252
0.8102	Intermediate Similarity	NPC199273
0.8099	Intermediate Similarity	NPC475627
0.8099	Intermediate Similarity	NPC476282
0.8099	Intermediate Similarity	NPC475457
0.8099	Intermediate Similarity	NPC475346
0.8099	Intermediate Similarity	NPC78307
0.8099	Intermediate Similarity	NPC18982
0.8095	Intermediate Similarity	NPC477209
0.8092	Intermediate Similarity	NPC124842
0.8082	Intermediate Similarity	NPC203063
0.8079	Intermediate Similarity	NPC142654
0.8074	Intermediate Similarity	NPC236520
0.8074	Intermediate Similarity	NPC294361
0.8071	Intermediate Similarity	NPC117899
0.8058	Intermediate Similarity	NPC107672
0.8056	Intermediate Similarity	NPC193358
0.8042	Intermediate Similarity	NPC477594
0.803	Intermediate Similarity	NPC322197
0.8026	Intermediate Similarity	NPC475454
0.8026	Intermediate Similarity	NPC473579
0.8026	Intermediate Similarity	NPC475311
0.8026	Intermediate Similarity	NPC473680
0.8025	Intermediate Similarity	NPC266365
0.8014	Intermediate Similarity	NPC472903
0.8	Intermediate Similarity	NPC470377
0.8	Intermediate Similarity	NPC3009
0.8	Intermediate Similarity	NPC190501
0.8	Intermediate Similarity	NPC318552
0.8	Intermediate Similarity	NPC36868
0.8	Intermediate Similarity	NPC290030
0.8	Intermediate Similarity	NPC471975
0.8	Intermediate Similarity	NPC478060
0.8	Intermediate Similarity	NPC193203
0.8	Intermediate Similarity	NPC478059
0.8	Intermediate Similarity	NPC470374
0.7987	Intermediate Similarity	NPC62051
0.7986	Intermediate Similarity	NPC95485
0.7986	Intermediate Similarity	NPC88065
0.7986	Intermediate Similarity	NPC89504
0.7973	Intermediate Similarity	NPC291078
0.7973	Intermediate Similarity	NPC193555
0.7972	Intermediate Similarity	NPC225051
0.7972	Intermediate Similarity	NPC53896
0.7972	Intermediate Similarity	NPC115458
0.7961	Intermediate Similarity	NPC327962
0.7959	Intermediate Similarity	NPC27518
0.7959	Intermediate Similarity	NPC304110
0.7956	Intermediate Similarity	NPC282577
0.7945	Intermediate Similarity	NPC182249
0.7945	Intermediate Similarity	NPC4214
0.7937	Intermediate Similarity	NPC200726
0.7933	Intermediate Similarity	NPC160777
0.7933	Intermediate Similarity	NPC73416
0.7931	Intermediate Similarity	NPC474311
0.7931	Intermediate Similarity	NPC65005
0.7931	Intermediate Similarity	NPC194764
0.7931	Intermediate Similarity	NPC264112
0.7931	Intermediate Similarity	NPC472308
0.7926	Intermediate Similarity	NPC42657
0.7919	Intermediate Similarity	NPC238629
0.7919	Intermediate Similarity	NPC25491
0.7917	Intermediate Similarity	NPC50924
0.7908	Intermediate Similarity	NPC118033
0.7908	Intermediate Similarity	NPC295977
0.7908	Intermediate Similarity	NPC58310
0.7905	Intermediate Similarity	NPC472904
0.7891	Intermediate Similarity	NPC473591
0.7891	Intermediate Similarity	NPC271494
0.7891	Intermediate Similarity	NPC155192
0.7888	Intermediate Similarity	NPC177362
0.7883	Intermediate Similarity	NPC154696
0.7881	Intermediate Similarity	NPC110882

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 NPC471974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	931
0.2-0.3	1463
0.3-0.4	2939
0.4-0.5	2234
0.5-0.6	940
0.6-0.7	262
0.7-0.8	8
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8531	High Similarity	NPD8166	Discontinued
0.8	Intermediate Similarity	NPD3019	Approved
0.7868	Intermediate Similarity	NPD2932	Approved
0.7815	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD943	Approved
0.766	Intermediate Similarity	NPD1470	Approved
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7568	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3026	Approved
0.7554	Intermediate Similarity	NPD3023	Approved
0.7536	Intermediate Similarity	NPD3024	Approved
0.7536	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3025	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.74	Intermediate Similarity	NPD5404	Approved
0.74	Intermediate Similarity	NPD5408	Approved
0.74	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD5405	Approved
0.7347	Intermediate Similarity	NPD6663	Approved
0.7338	Intermediate Similarity	NPD3300	Phase 2
0.7324	Intermediate Similarity	NPD9269	Phase 2
0.7324	Intermediate Similarity	NPD3972	Approved
0.732	Intermediate Similarity	NPD7003	Approved
0.731	Intermediate Similarity	NPD9494	Approved
0.731	Intermediate Similarity	NPD5736	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6273	Approved
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7174	Intermediate Similarity	NPD5951	Approved
0.7162	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD7610	Discontinued
0.7133	Intermediate Similarity	NPD3092	Approved
0.7133	Intermediate Similarity	NPD230	Phase 1
0.711	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7092	Intermediate Similarity	NPD3091	Approved
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3094	Phase 2
0.7055	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6190	Approved
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7042	Intermediate Similarity	NPD9268	Approved
0.7032	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7028	Phase 2
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD8032	Phase 2
0.6994	Remote Similarity	NPD2801	Approved
0.6993	Remote Similarity	NPD4059	Approved
0.6993	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4878	Approved
0.6962	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD3226	Approved
0.6954	Remote Similarity	NPD3620	Phase 2
0.6954	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD1755	Approved
0.6912	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3882	Suspended
0.6903	Remote Similarity	NPD2344	Approved
0.6897	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3020	Approved
0.6883	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD1512	Approved
0.6875	Remote Similarity	NPD3095	Discontinued
0.6871	Remote Similarity	NPD1876	Approved
0.6855	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2935	Discontinued
0.6839	Remote Similarity	NPD6099	Approved
0.6839	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6166	Phase 2
0.6824	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1164	Approved
0.6824	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5844	Phase 1
0.6795	Remote Similarity	NPD2346	Discontinued
0.6795	Remote Similarity	NPD1471	Phase 3
0.6792	Remote Similarity	NPD7236	Approved
0.6788	Remote Similarity	NPD1465	Phase 2
0.6788	Remote Similarity	NPD7819	Suspended
0.6783	Remote Similarity	NPD5536	Phase 2
0.6782	Remote Similarity	NPD7685	Pre-registration
0.678	Remote Similarity	NPD8150	Discontinued
0.6779	Remote Similarity	NPD257	Approved
0.6779	Remote Similarity	NPD258	Approved
0.6779	Remote Similarity	NPD2798	Approved
0.6776	Remote Similarity	NPD7961	Discontinued
0.6759	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1283	Approved
0.6755	Remote Similarity	NPD7095	Approved
0.6755	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7008	Discontinued
0.6748	Remote Similarity	NPD3455	Phase 2
0.6736	Remote Similarity	NPD9545	Approved
0.673	Remote Similarity	NPD2309	Approved
0.6728	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3268	Approved
0.6708	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4380	Phase 2
0.669	Remote Similarity	NPD1651	Approved
0.6688	Remote Similarity	NPD7266	Discontinued
0.6686	Remote Similarity	NPD5494	Approved
0.6685	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5978	Approved
0.6647	Remote Similarity	NPD3818	Discontinued
0.6647	Remote Similarity	NPD5977	Approved
0.6647	Remote Similarity	NPD6959	Discontinued
0.6646	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1607	Approved
0.6643	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6234	Discontinued
0.6623	Remote Similarity	NPD826	Approved
0.6623	Remote Similarity	NPD825	Approved
0.6623	Remote Similarity	NPD1240	Approved
0.6618	Remote Similarity	NPD1929	Approved
0.6618	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1930	Approved
0.661	Remote Similarity	NPD8312	Approved
0.661	Remote Similarity	NPD8313	Approved
0.6609	Remote Similarity	NPD7054	Approved
0.6607	Remote Similarity	NPD7768	Phase 2
0.6605	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2933	Approved
0.6591	Remote Similarity	NPD2934	Approved
0.6585	Remote Similarity	NPD7239	Suspended
0.6579	Remote Similarity	NPD2606	Approved
0.6579	Remote Similarity	NPD2605	Approved
0.6575	Remote Similarity	NPD4093	Discontinued
0.6573	Remote Similarity	NPD2629	Approved
0.6571	Remote Similarity	NPD7472	Approved
0.6568	Remote Similarity	NPD7075	Discontinued
0.6554	Remote Similarity	NPD1281	Approved
0.6552	Remote Similarity	NPD7228	Approved
0.6547	Remote Similarity	NPD2342	Discontinued
0.6541	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6651	Approved
0.6536	Remote Similarity	NPD5155	Approved
0.6536	Remote Similarity	NPD5156	Approved
0.6531	Remote Similarity	NPD1751	Approved
0.6527	Remote Similarity	NPD37	Approved
0.6527	Remote Similarity	NPD7577	Discontinued
0.6519	Remote Similarity	NPD2066	Phase 3
0.6514	Remote Similarity	NPD1221	Approved
0.6513	Remote Similarity	NPD9569	Approved
0.651	Remote Similarity	NPD1608	Approved
0.6507	Remote Similarity	NPD7009	Phase 2
0.6506	Remote Similarity	NPD6599	Discontinued
0.6503	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5283	Phase 1
0.65	Remote Similarity	NPD2800	Approved
0.6497	Remote Similarity	NPD5029	Approved
0.6497	Remote Similarity	NPD5027	Approved
0.6497	Remote Similarity	NPD5031	Approved
0.6497	Remote Similarity	NPD7251	Discontinued
0.6494	Remote Similarity	NPD2313	Discontinued
0.6494	Remote Similarity	NPD5033	Approved
0.6493	Remote Similarity	NPD288	Approved
0.6488	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4879	Approved
0.6481	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD228	Approved
0.6474	Remote Similarity	NPD275	Approved
0.6474	Remote Similarity	NPD447	Suspended
0.6474	Remote Similarity	NPD274	Approved
0.6474	Remote Similarity	NPD5735	Approved
0.6471	Remote Similarity	NPD3594	Approved
0.6471	Remote Similarity	NPD3595	Approved
0.6471	Remote Similarity	NPD3749	Approved
0.6471	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD4955	Approved
0.6461	Remote Similarity	NPD5034	Approved
0.6461	Remote Similarity	NPD5032	Approved
0.6461	Remote Similarity	NPD5028	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