NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	430.13
Volume:	406.943
LogP:	1.511
LogD:	-0.024
LogS:	-3.057
# Rotatable Bonds:	2
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.998
Fsp3:	0.409
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:	-6.307
MDCK Permeability:	6.204475084814476e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.692
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	90.09752655029297%
Volume Distribution (VD):	0.831
Pgp-substrate:	12.896612167358398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	1.409
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.855
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.825
Carcinogencity:	0.464
Eye Corrosion:	0.003
Eye Irritation:	0.24
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC478027

Natural Product ID:	NPC478027
*Common Name:**	2-[(1R,7S,9R,16R,18R,19R)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.02,15.04,13.06,11]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid
IUPAC Name:	2-[(1R,7S,9R,16R,18R,19R)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.02,15.04,13.06,11]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid
Synonyms:
Standard InCHIKey:	QJOFRWDMXPKWGM-AOYFJZKLSA-N
Standard InCHI:	InChI=1S/C22H22O9/c1-7-15-9(3-10(30-7)5-14(24)25)4-11-16(20(15)27)21(28)18-17(19(11)26)12-6-13(23)22(18,29)8(2)31-12/h4,7-8,10,12-13,23,27,29H,3,5-6H2,1-2H3,(H,24,25)/t7-,8+,10+,12+,13+,22-/m0/s1
SMILES:	C[C@H]1C2=C(C3=C(C=C2C[C@@H](O1)CC(=O)O)C(=O)C4=C(C3=O)[C@@]5([C@H](O[C@@H]4C[C@H]5O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118714008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO33516	Streptomyces sp. CPCC 200532	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25153802]

☑ 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	4

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	96600	nM	PMID[25153802]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	297300	nM	PMID[25153802]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	148000	nM	PMID[25153802]
NPT2	Others	Unspecified		IC50	=	178700	nM	PMID[25153802]

☑ 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 NPC478027 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	346
0.1-0.2	1319
0.2-0.3	2796
0.3-0.4	6002
0.4-0.5	10153
0.5-0.6	7668
0.6-0.7	6407
0.7-0.8	7415
0.8-0.85	490
0.85-0.9	97
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC478026
0.9	High Similarity	NPC103910
0.8968	High Similarity	NPC471695
0.8968	High Similarity	NPC474621
0.8968	High Similarity	NPC474622
0.8951	High Similarity	NPC470580
0.8938	High Similarity	NPC478020
0.8938	High Similarity	NPC478022
0.8902	High Similarity	NPC19056
0.8902	High Similarity	NPC470583
0.8854	High Similarity	NPC472050
0.8831	High Similarity	NPC44378
0.8831	High Similarity	NPC280753
0.8816	High Similarity	NPC474630
0.8797	High Similarity	NPC472889
0.8797	High Similarity	NPC208651
0.8797	High Similarity	NPC206641
0.8795	High Similarity	NPC470582
0.8795	High Similarity	NPC266513
0.8795	High Similarity	NPC470581
0.8795	High Similarity	NPC115447
0.8782	High Similarity	NPC474533
0.8782	High Similarity	NPC474534
0.878	High Similarity	NPC270027
0.878	High Similarity	NPC183441
0.8774	High Similarity	NPC477914
0.8766	High Similarity	NPC94781
0.8758	High Similarity	NPC285122
0.8726	High Similarity	NPC155686
0.8726	High Similarity	NPC478231
0.8726	High Similarity	NPC137301
0.8726	High Similarity	NPC312482
0.872	High Similarity	NPC478021
0.8704	High Similarity	NPC329647
0.8704	High Similarity	NPC470735
0.8696	High Similarity	NPC187934
0.8696	High Similarity	NPC97637
0.8684	High Similarity	NPC21873
0.8683	High Similarity	NPC83331
0.8679	High Similarity	NPC29552
0.8671	High Similarity	NPC478230
0.8671	High Similarity	NPC174599
0.8671	High Similarity	NPC192219
0.8671	High Similarity	NPC82190
0.8671	High Similarity	NPC472890
0.8671	High Similarity	NPC478221
0.8671	High Similarity	NPC69043
0.8671	High Similarity	NPC3449
0.8667	High Similarity	NPC294501
0.8667	High Similarity	NPC295339
0.8662	High Similarity	NPC478224
0.8662	High Similarity	NPC115249
0.8636	High Similarity	NPC473023
0.8636	High Similarity	NPC120536
0.8631	High Similarity	NPC283980
0.8631	High Similarity	NPC187441
0.8623	High Similarity	NPC176246
0.8616	High Similarity	NPC148323
0.8616	High Similarity	NPC283480
0.8614	High Similarity	NPC472054
0.8608	High Similarity	NPC182921
0.8608	High Similarity	NPC218870
0.8608	High Similarity	NPC470408
0.8608	High Similarity	NPC474824
0.86	High Similarity	NPC61590
0.86	High Similarity	NPC197666
0.86	High Similarity	NPC126739
0.8599	High Similarity	NPC46882
0.8599	High Similarity	NPC132990
0.8598	High Similarity	NPC234497
0.8598	High Similarity	NPC107009
0.8598	High Similarity	NPC472058
0.8598	High Similarity	NPC470341
0.8598	High Similarity	NPC105414
0.8598	High Similarity	NPC324522
0.8598	High Similarity	NPC473094
0.8591	High Similarity	NPC315275
0.859	High Similarity	NPC120171
0.8589	High Similarity	NPC472057
0.8589	High Similarity	NPC472051
0.8581	High Similarity	NPC53362
0.8581	High Similarity	NPC166583
0.8571	High Similarity	NPC170055
0.8571	High Similarity	NPC477683
0.8571	High Similarity	NPC472055
0.8571	High Similarity	NPC477682
0.8563	High Similarity	NPC294149
0.8563	High Similarity	NPC68381
0.8562	High Similarity	NPC471731
0.8562	High Similarity	NPC159721
0.8562	High Similarity	NPC246466
0.8562	High Similarity	NPC478225
0.8554	High Similarity	NPC473113
0.8554	High Similarity	NPC472620
0.8553	High Similarity	NPC471456
0.8553	High Similarity	NPC317585
0.8553	High Similarity	NPC257003
0.8553	High Similarity	NPC170189
0.8553	High Similarity	NPC208173
0.8545	High Similarity	NPC473095
0.8545	High Similarity	NPC175477
0.8545	High Similarity	NPC473096
0.8545	High Similarity	NPC191653
0.8544	High Similarity	NPC184284
0.8544	High Similarity	NPC76041
0.8537	High Similarity	NPC178173
0.8535	High Similarity	NPC472891
0.8526	High Similarity	NPC470479
0.8519	High Similarity	NPC117985
0.8516	High Similarity	NPC136878
0.8509	High Similarity	NPC53139
0.8509	High Similarity	NPC470339
0.8506	High Similarity	NPC29932
0.8506	High Similarity	NPC84568
0.8506	High Similarity	NPC300684
0.8506	High Similarity	NPC48130
0.8506	High Similarity	NPC151607
0.8506	High Similarity	NPC42540
0.8506	High Similarity	NPC218866
0.8503	High Similarity	NPC65118
0.8503	High Similarity	NPC154986
0.85	High Similarity	NPC474861
0.8497	Intermediate Similarity	NPC471733
0.8491	Intermediate Similarity	NPC209393
0.8491	Intermediate Similarity	NPC205172
0.8485	Intermediate Similarity	NPC63470
0.8481	Intermediate Similarity	NPC205918
0.8481	Intermediate Similarity	NPC70016
0.8481	Intermediate Similarity	NPC215921
0.8476	Intermediate Similarity	NPC178281
0.8471	Intermediate Similarity	NPC237440
0.8471	Intermediate Similarity	NPC475161
0.8471	Intermediate Similarity	NPC478219
0.8471	Intermediate Similarity	NPC477860
0.8471	Intermediate Similarity	NPC208069
0.8471	Intermediate Similarity	NPC270160
0.8466	Intermediate Similarity	NPC472059
0.8462	Intermediate Similarity	NPC119767
0.8452	Intermediate Similarity	NPC474309
0.8452	Intermediate Similarity	NPC70862
0.8447	Intermediate Similarity	NPC478226
0.8447	Intermediate Similarity	NPC263483
0.8443	Intermediate Similarity	NPC271385
0.8443	Intermediate Similarity	NPC5029
0.8443	Intermediate Similarity	NPC76128
0.8443	Intermediate Similarity	NPC111536
0.8443	Intermediate Similarity	NPC30432
0.8442	Intermediate Similarity	NPC476473
0.8438	Intermediate Similarity	NPC266469
0.8438	Intermediate Similarity	NPC66029
0.8434	Intermediate Similarity	NPC472619
0.8431	Intermediate Similarity	NPC472604
0.8431	Intermediate Similarity	NPC472603
0.8431	Intermediate Similarity	NPC472605
0.8431	Intermediate Similarity	NPC149533
0.8428	Intermediate Similarity	NPC256141
0.8428	Intermediate Similarity	NPC470340
0.8428	Intermediate Similarity	NPC478220
0.8424	Intermediate Similarity	NPC477835
0.8424	Intermediate Similarity	NPC20237
0.8421	Intermediate Similarity	NPC111422
0.8421	Intermediate Similarity	NPC476477
0.8421	Intermediate Similarity	NPC306835
0.8421	Intermediate Similarity	NPC299405
0.8421	Intermediate Similarity	NPC216312
0.8421	Intermediate Similarity	NPC471602
0.8421	Intermediate Similarity	NPC256463
0.8421	Intermediate Similarity	NPC29771
0.8418	Intermediate Similarity	NPC205766
0.8418	Intermediate Similarity	NPC56204
0.8415	Intermediate Similarity	NPC249181
0.8415	Intermediate Similarity	NPC472053
0.8412	Intermediate Similarity	NPC72783
0.8408	Intermediate Similarity	NPC112816
0.8405	Intermediate Similarity	NPC317544
0.8405	Intermediate Similarity	NPC472261
0.8402	Intermediate Similarity	NPC324220
0.8402	Intermediate Similarity	NPC312630
0.8402	Intermediate Similarity	NPC475233
0.8402	Intermediate Similarity	NPC475246
0.8402	Intermediate Similarity	NPC46958
0.84	Intermediate Similarity	NPC27407
0.84	Intermediate Similarity	NPC142027
0.8397	Intermediate Similarity	NPC470570
0.8397	Intermediate Similarity	NPC147250
0.8395	Intermediate Similarity	NPC314795
0.8393	Intermediate Similarity	NPC85368
0.8391	Intermediate Similarity	NPC314672
0.8385	Intermediate Similarity	NPC478223
0.8383	Intermediate Similarity	NPC298778
0.8383	Intermediate Similarity	NPC313304
0.8377	Intermediate Similarity	NPC474300
0.8377	Intermediate Similarity	NPC322112
0.8377	Intermediate Similarity	NPC82913
0.8377	Intermediate Similarity	NPC314271
0.8375	Intermediate Similarity	NPC192189
0.8373	Intermediate Similarity	NPC283041
0.8366	Intermediate Similarity	NPC241349
0.8366	Intermediate Similarity	NPC147542
0.8366	Intermediate Similarity	NPC32749

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 NPC478027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	864
0.2-0.3	1680
0.3-0.4	2637
0.4-0.5	2133
0.5-0.6	1039
0.6-0.7	365
0.7-0.8	132
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD8150	Discontinued
0.8382	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD4380	Phase 2
0.8101	Intermediate Similarity	NPD2533	Approved
0.8101	Intermediate Similarity	NPD2532	Approved
0.8101	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD6535	Approved
0.8079	Intermediate Similarity	NPD6534	Approved
0.8024	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7977	Intermediate Similarity	NPD8313	Approved
0.7977	Intermediate Similarity	NPD8312	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7955	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7699	Phase 2
0.7944	Intermediate Similarity	NPD7700	Phase 2
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7923	Intermediate Similarity	NPD7435	Discontinued
0.7901	Intermediate Similarity	NPD3226	Approved
0.7892	Intermediate Similarity	NPD7075	Discontinued
0.788	Intermediate Similarity	NPD8319	Approved
0.788	Intermediate Similarity	NPD8320	Phase 1
0.7857	Intermediate Similarity	NPD6780	Approved
0.7857	Intermediate Similarity	NPD6776	Approved
0.7857	Intermediate Similarity	NPD6782	Approved
0.7857	Intermediate Similarity	NPD6779	Approved
0.7857	Intermediate Similarity	NPD6778	Approved
0.7857	Intermediate Similarity	NPD6777	Approved
0.7857	Intermediate Similarity	NPD6781	Approved
0.7821	Intermediate Similarity	NPD6212	Phase 3
0.7821	Intermediate Similarity	NPD6213	Phase 3
0.7821	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7756	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5406	Approved
0.7707	Intermediate Similarity	NPD5404	Approved
0.7707	Intermediate Similarity	NPD5405	Approved
0.7707	Intermediate Similarity	NPD5408	Approved
0.7702	Intermediate Similarity	NPD7390	Discontinued
0.7688	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7874	Approved
0.7672	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5402	Approved
0.7657	Intermediate Similarity	NPD6559	Discontinued
0.7634	Intermediate Similarity	NPD7697	Approved
0.7634	Intermediate Similarity	NPD7696	Phase 3
0.7634	Intermediate Similarity	NPD7698	Approved
0.7619	Intermediate Similarity	NPD8151	Discontinued
0.7616	Intermediate Similarity	NPD6166	Phase 2
0.7616	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD5710	Approved
0.7594	Intermediate Similarity	NPD7871	Phase 2
0.7594	Intermediate Similarity	NPD7870	Phase 2
0.759	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD7054	Approved
0.7566	Intermediate Similarity	NPD7701	Phase 2
0.7546	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1934	Approved
0.7543	Intermediate Similarity	NPD7074	Phase 3
0.7543	Intermediate Similarity	NPD7472	Approved
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7487	Intermediate Similarity	NPD6823	Phase 2
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.747	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7251	Discontinued
0.7456	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3817	Phase 2
0.7455	Intermediate Similarity	NPD5403	Approved
0.7452	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD7801	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7419	Intermediate Similarity	NPD8285	Discontinued
0.7416	Intermediate Similarity	NPD7808	Phase 3
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3750	Approved
0.7396	Intermediate Similarity	NPD2801	Approved
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7386	Intermediate Similarity	NPD1470	Approved
0.7384	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD3749	Approved
0.7362	Intermediate Similarity	NPD6190	Approved
0.7358	Intermediate Similarity	NPD7783	Phase 2
0.7358	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5401	Approved
0.7326	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1510	Phase 2
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD6799	Approved
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD3764	Approved
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2800	Approved
0.7232	Intermediate Similarity	NPD7228	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3300	Phase 2
0.7209	Intermediate Similarity	NPD7768	Phase 2
0.7209	Intermediate Similarity	NPD3882	Suspended
0.72	Intermediate Similarity	NPD3787	Discontinued
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.7188	Intermediate Similarity	NPD1607	Approved
0.7169	Intermediate Similarity	NPD1511	Approved
0.7167	Intermediate Similarity	NPD7685	Pre-registration
0.716	Intermediate Similarity	NPD2796	Approved
0.7135	Intermediate Similarity	NPD37	Approved
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7124	Intermediate Similarity	NPD1201	Approved
0.711	Intermediate Similarity	NPD4966	Approved
0.711	Intermediate Similarity	NPD4965	Approved
0.711	Intermediate Similarity	NPD4967	Phase 2
0.7108	Intermediate Similarity	NPD7236	Approved
0.7101	Intermediate Similarity	NPD7239	Suspended
0.7099	Intermediate Similarity	NPD2799	Discontinued
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3748	Approved
0.7091	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD9545	Approved
0.7083	Intermediate Similarity	NPD1512	Approved
0.7081	Intermediate Similarity	NPD6651	Approved
0.7067	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD9493	Approved
0.7063	Intermediate Similarity	NPD943	Approved
0.7063	Intermediate Similarity	NPD1240	Approved
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7044	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD920	Approved
0.7019	Intermediate Similarity	NPD447	Suspended
0.7017	Intermediate Similarity	NPD5953	Discontinued
0.7012	Intermediate Similarity	NPD7266	Discontinued
0.6994	Remote Similarity	NPD8455	Phase 2
0.6994	Remote Similarity	NPD7033	Discontinued
0.6981	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8368	Discontinued
0.6957	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7177	Discontinued
0.6942	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8059	Phase 3
0.694	Remote Similarity	NPD5034	Approved
0.694	Remote Similarity	NPD4955	Approved
0.694	Remote Similarity	NPD5026	Approved
0.694	Remote Similarity	NPD4954	Approved
0.694	Remote Similarity	NPD5028	Approved
0.694	Remote Similarity	NPD36	Approved
0.6937	Remote Similarity	NPD7985	Registered
0.6932	Remote Similarity	NPD919	Approved
0.6928	Remote Similarity	NPD1243	Approved
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5124	Phase 1
0.6914	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8360	Approved
0.6898	Remote Similarity	NPD8361	Approved
0.689	Remote Similarity	NPD4308	Phase 3
0.6885	Remote Similarity	NPD5030	Phase 2
0.6885	Remote Similarity	NPD7240	Approved
0.6882	Remote Similarity	NPD5037	Approved
0.6882	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD5038	Approved
0.6865	Remote Similarity	NPD8407	Phase 2
0.6848	Remote Similarity	NPD2438	Suspended
0.6835	Remote Similarity	NPD1164	Approved
0.6832	Remote Similarity	NPD411	Approved
0.6828	Remote Similarity	NPD5036	Approved
0.6816	Remote Similarity	NPD7930	Approved
0.6813	Remote Similarity	NPD7286	Phase 2
0.6813	Remote Similarity	NPD6832	Phase 2
0.6811	Remote Similarity	NPD5035	Approved
0.6809	Remote Similarity	NPD8435	Approved
0.6807	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2344	Approved
0.6805	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7584	Approved
0.68	Remote Similarity	NPD5760	Phase 2

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