NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	410.17
Volume:	415.164
LogP:	4.298
LogD:	3.369
LogS:	-4.774
# Rotatable Bonds:	3
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	6.227
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	1.587829137861263e-05
Pgp-inhibitor:	0.222
Pgp-substrate:	0.267
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.535
30% Bioavailability (F30%):	0.834

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	90.76211547851562%
Volume Distribution (VD):	1.587
Pgp-substrate:	9.23155403137207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.253
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.597
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	11.596
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.941
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.663
Carcinogencity:	0.944
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC476929

Natural Product ID:	NPC476929
*Common Name:**	(1S,12R,13S,16R)-7-hydroxy-12-methoxy-15,15-dimethyl-13-(3-methylbut-2-enyl)-2,14-dioxapentacyclo[11.4.1.01,10.03,8.012,16]octadeca-3,5,7,10-tetraene-9,18-dione
IUPAC Name:	(1S,12R,13S,16R)-7-hydroxy-12-methoxy-15,15-dimethyl-13-(3-methylbut-2-enyl)-2,14-dioxapentacyclo[11.4.1.01,10.03,8.012,16]octadeca-3,5,7,10-tetraene-9,18-dione
Synonyms:
Standard InCHIKey:	AVKWWEJYPMZXJR-TXCSNJEZSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-13(2)9-10-23-20(27)22-12-17(21(3,4)30-23)24(23,28-5)11-14(22)19(26)18-15(25)7-6-8-16(18)29-22/h6-9,11,17,25H,10,12H2,1-5H3/t17-,22+,23-,24-/m1/s1
SMILES:	CC(=CC[C@@]12C(=O)[C@]34C[C@@H]([C@@]1(C=C3C(=O)C5=C(C=CC=C5O4)O)OC)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118707563
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	roots	n.a.	n.a.	PMID[24940955]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5	ug/ml	PMID[24940955]

☑ 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 NPC476929 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	429
0.1-0.2	1528
0.2-0.3	3012
0.3-0.4	7231
0.4-0.5	10748
0.5-0.6	5360
0.6-0.7	5905
0.7-0.8	7218
0.8-0.85	1164
0.85-0.9	65
0.9-0.95	32
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC476931
0.9427	High Similarity	NPC475106
0.9371	High Similarity	NPC62444
0.9299	High Similarity	NPC43490
0.9299	High Similarity	NPC475107
0.9193	High Similarity	NPC193222
0.9182	High Similarity	NPC94796
0.9141	High Similarity	NPC118128
0.913	High Similarity	NPC476255
0.913	High Similarity	NPC476056
0.9051	High Similarity	NPC476930
0.8994	High Similarity	NPC125969
0.8987	High Similarity	NPC164427
0.897	High Similarity	NPC476152
0.897	High Similarity	NPC475080
0.8938	High Similarity	NPC286422
0.8917	High Similarity	NPC275878
0.8909	High Similarity	NPC476159
0.8909	High Similarity	NPC477529
0.8889	High Similarity	NPC131578
0.8875	High Similarity	NPC311574
0.8875	High Similarity	NPC264932
0.8861	High Similarity	NPC311579
0.8861	High Similarity	NPC236756
0.8855	High Similarity	NPC476139
0.8855	High Similarity	NPC476229
0.8854	High Similarity	NPC207346
0.8854	High Similarity	NPC46564
0.8854	High Similarity	NPC471229
0.8848	High Similarity	NPC315306
0.8848	High Similarity	NPC313717
0.8841	High Similarity	NPC150131
0.8841	High Similarity	NPC223413
0.8834	High Similarity	NPC314653
0.8834	High Similarity	NPC316262
0.882	High Similarity	NPC172687
0.8812	High Similarity	NPC161650
0.8812	High Similarity	NPC210048
0.8805	High Similarity	NPC326910
0.8805	High Similarity	NPC476169
0.8805	High Similarity	NPC175192
0.8797	High Similarity	NPC288534
0.8797	High Similarity	NPC473996
0.8797	High Similarity	NPC210597
0.8795	High Similarity	NPC169018
0.879	High Similarity	NPC267117
0.8788	High Similarity	NPC40089
0.8788	High Similarity	NPC63514
0.8788	High Similarity	NPC158329
0.8788	High Similarity	NPC476146
0.8788	High Similarity	NPC152477
0.8782	High Similarity	NPC296869
0.8774	High Similarity	NPC470676
0.8774	High Similarity	NPC473132
0.8774	High Similarity	NPC473135
0.8774	High Similarity	NPC477955
0.8757	High Similarity	NPC244903
0.8743	High Similarity	NPC147363
0.8743	High Similarity	NPC73899
0.8743	High Similarity	NPC476311
0.8743	High Similarity	NPC469393
0.8743	High Similarity	NPC474276
0.8743	High Similarity	NPC17105
0.8742	High Similarity	NPC203080
0.8742	High Similarity	NPC100134
0.8742	High Similarity	NPC209760
0.8735	High Similarity	NPC476196
0.8735	High Similarity	NPC101107
0.8734	High Similarity	NPC305965
0.8734	High Similarity	NPC472580
0.8734	High Similarity	NPC472636
0.8734	High Similarity	NPC476162
0.8727	High Similarity	NPC292233
0.8727	High Similarity	NPC126204
0.8726	High Similarity	NPC277032
0.872	High Similarity	NPC234052
0.872	High Similarity	NPC472049
0.872	High Similarity	NPC189689
0.8718	High Similarity	NPC472918
0.8712	High Similarity	NPC229632
0.8712	High Similarity	NPC472402
0.8704	High Similarity	NPC313368
0.8698	High Similarity	NPC476199
0.8698	High Similarity	NPC246877
0.8698	High Similarity	NPC476210
0.8696	High Similarity	NPC67876
0.8696	High Similarity	NPC201127
0.8696	High Similarity	NPC181960
0.869	High Similarity	NPC162248
0.869	High Similarity	NPC245975
0.8688	High Similarity	NPC31018
0.8688	High Similarity	NPC255807
0.8688	High Similarity	NPC217706
0.8688	High Similarity	NPC471116
0.8688	High Similarity	NPC207809
0.8688	High Similarity	NPC259710
0.8688	High Similarity	NPC48579
0.8688	High Similarity	NPC304207
0.8683	High Similarity	NPC121333
0.8679	High Similarity	NPC171651
0.8679	High Similarity	NPC327269
0.8679	High Similarity	NPC476238
0.8679	High Similarity	NPC216035
0.8679	High Similarity	NPC321363
0.8679	High Similarity	NPC243171
0.8679	High Similarity	NPC477957
0.8679	High Similarity	NPC217149
0.8679	High Similarity	NPC253904
0.8679	High Similarity	NPC35567
0.8679	High Similarity	NPC31627
0.8679	High Similarity	NPC142527
0.8675	High Similarity	NPC54903
0.8675	High Similarity	NPC475805
0.8675	High Similarity	NPC75141
0.8675	High Similarity	NPC55422
0.8675	High Similarity	NPC286074
0.8675	High Similarity	NPC242395
0.8675	High Similarity	NPC476216
0.8675	High Similarity	NPC41598
0.8675	High Similarity	NPC47634
0.8671	High Similarity	NPC472421
0.8671	High Similarity	NPC471115
0.8671	High Similarity	NPC475717
0.8671	High Similarity	NPC29777
0.8667	High Similarity	NPC173292
0.8667	High Similarity	NPC235610
0.8667	High Similarity	NPC477517
0.8667	High Similarity	NPC475109
0.8667	High Similarity	NPC128293
0.8662	High Similarity	NPC39195
0.8662	High Similarity	NPC244407
0.8662	High Similarity	NPC191634
0.8659	High Similarity	NPC469395
0.8659	High Similarity	NPC273959
0.8659	High Similarity	NPC159508
0.8659	High Similarity	NPC472582
0.8654	High Similarity	NPC178343
0.8654	High Similarity	NPC299011
0.8654	High Similarity	NPC196114
0.8654	High Similarity	NPC229190
0.8654	High Similarity	NPC329678
0.8654	High Similarity	NPC306488
0.8654	High Similarity	NPC5820
0.8654	High Similarity	NPC124729
0.865	High Similarity	NPC478134
0.865	High Similarity	NPC61382
0.865	High Similarity	NPC103816
0.8647	High Similarity	NPC473607
0.8645	High Similarity	NPC18585
0.8645	High Similarity	NPC106985
0.8645	High Similarity	NPC166138
0.8642	High Similarity	NPC152904
0.8642	High Similarity	NPC195832
0.8642	High Similarity	NPC55738
0.8639	High Similarity	NPC98943
0.8636	High Similarity	NPC232021
0.8636	High Similarity	NPC40118
0.8636	High Similarity	NPC126534
0.8634	High Similarity	NPC20530
0.8634	High Similarity	NPC215917
0.8634	High Similarity	NPC471500
0.8634	High Similarity	NPC10754
0.8634	High Similarity	NPC146636
0.8631	High Similarity	NPC154986
0.8631	High Similarity	NPC65885
0.8625	High Similarity	NPC223701
0.8625	High Similarity	NPC293286
0.8625	High Similarity	NPC178964
0.8625	High Similarity	NPC248793
0.8625	High Similarity	NPC180301
0.8625	High Similarity	NPC95842
0.8625	High Similarity	NPC7989
0.8625	High Similarity	NPC472583
0.8625	High Similarity	NPC280530
0.8625	High Similarity	NPC141212
0.8625	High Similarity	NPC189130
0.8623	High Similarity	NPC102277
0.8623	High Similarity	NPC279209
0.8623	High Similarity	NPC476641
0.8616	High Similarity	NPC81474
0.8616	High Similarity	NPC262039
0.8616	High Similarity	NPC254412
0.8616	High Similarity	NPC319910
0.8616	High Similarity	NPC471675
0.8616	High Similarity	NPC278476
0.8616	High Similarity	NPC471676
0.8616	High Similarity	NPC295650
0.8616	High Similarity	NPC474772
0.8616	High Similarity	NPC473131
0.8616	High Similarity	NPC244577
0.8616	High Similarity	NPC263384
0.8616	High Similarity	NPC472420
0.8616	High Similarity	NPC472422
0.8616	High Similarity	NPC262038
0.8616	High Similarity	NPC474744
0.8616	High Similarity	NPC470675
0.8616	High Similarity	NPC472423
0.8616	High Similarity	NPC236769
0.8614	High Similarity	NPC225419
0.8614	High Similarity	NPC476459

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 NPC476929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	883
0.2-0.3	1683
0.3-0.4	2634
0.4-0.5	2029
0.5-0.6	1027
0.6-0.7	373
0.7-0.8	158
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8519	High Similarity	NPD3882	Suspended
0.8476	Intermediate Similarity	NPD5494	Approved
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8395	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8282	Intermediate Similarity	NPD2801	Approved
0.8274	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8205	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD1512	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD7819	Suspended
0.8141	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3749	Approved
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3817	Phase 2
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.811	Intermediate Similarity	NPD6801	Discontinued
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.807	Intermediate Similarity	NPD3751	Discontinued
0.8068	Intermediate Similarity	NPD8434	Phase 2
0.8063	Intermediate Similarity	NPD1511	Approved
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8047	Intermediate Similarity	NPD6232	Discontinued
0.8038	Intermediate Similarity	NPD2800	Approved
0.8035	Intermediate Similarity	NPD6797	Phase 2
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.8012	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7965	Intermediate Similarity	NPD3818	Discontinued
0.7962	Intermediate Similarity	NPD6100	Approved
0.7962	Intermediate Similarity	NPD2796	Approved
0.7962	Intermediate Similarity	NPD6099	Approved
0.7943	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7808	Phase 3
0.7914	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD1247	Approved
0.7875	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7074	Phase 3
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7054	Approved
0.7791	Intermediate Similarity	NPD5401	Approved
0.7771	Intermediate Similarity	NPD7472	Approved
0.7765	Intermediate Similarity	NPD919	Approved
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7746	Intermediate Similarity	NPD2403	Approved
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7711	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD1471	Phase 3
0.7673	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD8150	Discontinued
0.7633	Intermediate Similarity	NPD1465	Phase 2
0.7627	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD2935	Discontinued
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7562	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6651	Approved
0.7542	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7698	Approved
0.7455	Intermediate Similarity	NPD3300	Phase 2
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD5710	Approved
0.7429	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5761	Phase 2
0.7427	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD7390	Discontinued
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD4749	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD943	Approved
0.7297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD7801	Approved
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6765	Approved
0.7293	Intermediate Similarity	NPD6764	Approved
0.7273	Intermediate Similarity	NPD7199	Phase 2
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD2798	Approved
0.7257	Intermediate Similarity	NPD6234	Discontinued
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD4287	Approved
0.7197	Intermediate Similarity	NPD1470	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD3268	Approved
0.717	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7228	Approved
0.7165	Intermediate Similarity	NPD8320	Phase 1
0.7165	Intermediate Similarity	NPD8319	Approved
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7907	Approved
0.7135	Intermediate Similarity	NPD6785	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7135	Intermediate Similarity	NPD6784	Approved
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7129	Intermediate Similarity	NPD4665	Approved
0.7129	Intermediate Similarity	NPD4111	Phase 1
0.7115	Intermediate Similarity	NPD9717	Approved
0.7107	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7105	Intermediate Similarity	NPD4361	Phase 2
0.7105	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7099	Intermediate Similarity	NPD1613	Approved
0.7089	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.7081	Intermediate Similarity	NPD3764	Approved
0.7066	Intermediate Similarity	NPD2654	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7062	Intermediate Similarity	NPD6823	Phase 2
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5124	Phase 1
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1201	Approved
0.7041	Intermediate Similarity	NPD7236	Approved
0.703	Intermediate Similarity	NPD8404	Phase 2
0.7024	Intermediate Similarity	NPD7003	Approved
0.7018	Intermediate Similarity	NPD6273	Approved
0.701	Intermediate Similarity	NPD2493	Approved
0.701	Intermediate Similarity	NPD2494	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