NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	410.17
Volume:	415.164
LogP:	4.538
LogD:	3.209
LogS:	-4.909
# 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:	6.058
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:	-4.665
MDCK Permeability:	2.2067340978537686e-05
Pgp-inhibitor:	0.246
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.767
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	92.45673370361328%
Volume Distribution (VD):	1.79
Pgp-substrate:	7.388366222381592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.214
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.464
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.576
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	14.203
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.864
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.891
Carcinogencity:	0.973
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC476931

Natural Product ID:	NPC476931
*Common Name:**	(1S,2S,13S,15S)-8-hydroxy-13-methoxy-17,17-dimethyl-15-(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
IUPAC Name:	(1S,2S,13S,15S)-8-hydroxy-13-methoxy-17,17-dimethyl-15-(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
Synonyms:
Standard InCHIKey:	XWFNYKWKDWAAMZ-QKBJRNKPSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-13(2)9-10-23-20(27)22(28-5)11-14-19(26)18-15(25)7-6-8-16(18)29-24(14,23)17(12-22)21(3,4)30-23/h6-9,11,17,25H,10,12H2,1-5H3/t17-,22+,23+,24+/m0/s1
SMILES:	CC(=CC[C@@]12C(=O)[C@@]3(C[C@H]([C@]14C(=C3)C(=O)C5=C(C=CC=C5O4)O)C(O2)(C)C)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118707564
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	=	0.36	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 NPC476931 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	435
0.1-0.2	1555
0.2-0.3	3115
0.3-0.4	7342
0.4-0.5	10592
0.5-0.6	5498
0.6-0.7	5793
0.7-0.8	7210
0.8-0.85	1061
0.85-0.9	42
0.9-0.95	38
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC62444
0.9677	High Similarity	NPC475107
0.9677	High Similarity	NPC43490
0.9615	High Similarity	NPC476929
0.956	High Similarity	NPC193222
0.9554	High Similarity	NPC94796
0.9497	High Similarity	NPC476056
0.9497	High Similarity	NPC476255
0.9325	High Similarity	NPC475080
0.9304	High Similarity	NPC286422
0.9299	High Similarity	NPC476930
0.9264	High Similarity	NPC476159
0.9264	High Similarity	NPC118128
0.925	High Similarity	NPC131578
0.9207	High Similarity	NPC476229
0.9198	High Similarity	NPC223413
0.9146	High Similarity	NPC169018
0.9091	High Similarity	NPC476152
0.9091	High Similarity	NPC476139
0.9074	High Similarity	NPC189689
0.9068	High Similarity	NPC475106
0.9024	High Similarity	NPC75141
0.9024	High Similarity	NPC47634
0.9024	High Similarity	NPC55422
0.9018	High Similarity	NPC475109
0.8982	High Similarity	NPC98943
0.8929	High Similarity	NPC233978
0.8909	High Similarity	NPC476146
0.8909	High Similarity	NPC476216
0.8909	High Similarity	NPC40089
0.8909	High Similarity	NPC63514
0.8909	High Similarity	NPC158329
0.8882	High Similarity	NPC125969
0.8875	High Similarity	NPC164427
0.8862	High Similarity	NPC476311
0.8861	High Similarity	NPC476162
0.8855	High Similarity	NPC476196
0.8817	High Similarity	NPC476199
0.8817	High Similarity	NPC476210
0.881	High Similarity	NPC162248
0.8805	High Similarity	NPC275878
0.8795	High Similarity	NPC41598
0.8765	High Similarity	NPC473607
0.8742	High Similarity	NPC471229
0.8742	High Similarity	NPC207346
0.8742	High Similarity	NPC46564
0.8706	High Similarity	NPC5671
0.8704	High Similarity	NPC201127
0.8698	High Similarity	NPC245975
0.8698	High Similarity	NPC475398
0.8696	High Similarity	NPC326910
0.8696	High Similarity	NPC476169
0.8696	High Similarity	NPC175192
0.869	High Similarity	NPC477529
0.8688	High Similarity	NPC210597
0.8688	High Similarity	NPC288534
0.8683	High Similarity	NPC152477
0.8679	High Similarity	NPC267117
0.8671	High Similarity	NPC191634
0.8667	High Similarity	NPC472581
0.8655	High Similarity	NPC473729
0.8655	High Similarity	NPC476273
0.865	High Similarity	NPC311574
0.865	High Similarity	NPC264932
0.8647	High Similarity	NPC227275
0.8639	High Similarity	NPC469393
0.8634	High Similarity	NPC236756
0.8634	High Similarity	NPC209760
0.8634	High Similarity	NPC311579
0.8634	High Similarity	NPC203080
0.8634	High Similarity	NPC100134
0.8631	High Similarity	NPC313717
0.8631	High Similarity	NPC315306
0.8623	High Similarity	NPC150131
0.8616	High Similarity	NPC277032
0.8614	High Similarity	NPC316262
0.8614	High Similarity	NPC234052
0.8614	High Similarity	NPC314653
0.8613	High Similarity	NPC476170
0.8606	High Similarity	NPC472402
0.8606	High Similarity	NPC229632
0.8606	High Similarity	NPC219861
0.8598	High Similarity	NPC313368
0.8598	High Similarity	NPC172687
0.8596	High Similarity	NPC221820
0.8589	High Similarity	NPC181960
0.8589	High Similarity	NPC474637
0.8589	High Similarity	NPC161650
0.8589	High Similarity	NPC210048
0.858	High Similarity	NPC255807
0.858	High Similarity	NPC31018
0.858	High Similarity	NPC121333
0.858	High Similarity	NPC471116
0.8571	High Similarity	NPC321363
0.8571	High Similarity	NPC473996
0.8571	High Similarity	NPC286074
0.8571	High Similarity	NPC253904
0.8571	High Similarity	NPC54903
0.8571	High Similarity	NPC242395
0.8563	High Similarity	NPC477517
0.8563	High Similarity	NPC235610
0.8563	High Similarity	NPC173292
0.8563	High Similarity	NPC128293
0.8562	High Similarity	NPC475717
0.8562	High Similarity	NPC471115
0.8562	High Similarity	NPC29777
0.8555	High Similarity	NPC8927
0.8554	High Similarity	NPC469395
0.8554	High Similarity	NPC109180
0.8554	High Similarity	NPC273959
0.8554	High Similarity	NPC159508
0.8553	High Similarity	NPC39195
0.8553	High Similarity	NPC296869
0.8547	High Similarity	NPC244903
0.8545	High Similarity	NPC478134
0.8545	High Similarity	NPC61382
0.8545	High Similarity	NPC103816
0.8544	High Similarity	NPC473132
0.8544	High Similarity	NPC477955
0.8544	High Similarity	NPC299011
0.8544	High Similarity	NPC473135
0.8544	High Similarity	NPC470676
0.8544	High Similarity	NPC329678
0.8537	High Similarity	NPC152904
0.8537	High Similarity	NPC55738
0.8537	High Similarity	NPC195832
0.8529	High Similarity	NPC17105
0.8529	High Similarity	NPC154986
0.8529	High Similarity	NPC147363
0.8529	High Similarity	NPC65885
0.8529	High Similarity	NPC73899
0.8529	High Similarity	NPC474276
0.8528	High Similarity	NPC146636
0.8521	High Similarity	NPC476641
0.8521	High Similarity	NPC28042
0.8521	High Similarity	NPC101107
0.8519	High Similarity	NPC178964
0.8519	High Similarity	NPC280530
0.8519	High Similarity	NPC95842
0.8512	High Similarity	NPC292233
0.8512	High Similarity	NPC478060
0.8512	High Similarity	NPC225419
0.8512	High Similarity	NPC471975
0.8512	High Similarity	NPC470377
0.8512	High Similarity	NPC470374
0.8512	High Similarity	NPC126204
0.8512	High Similarity	NPC478059
0.8512	High Similarity	NPC476459
0.8509	High Similarity	NPC472580
0.8509	High Similarity	NPC472636
0.8509	High Similarity	NPC305965
0.8503	High Similarity	NPC275780
0.8503	High Similarity	NPC224280
0.8503	High Similarity	NPC472049
0.8503	High Similarity	NPC472450
0.8503	High Similarity	NPC239752
0.8503	High Similarity	NPC62261
0.85	High Similarity	NPC266499
0.8494	Intermediate Similarity	NPC474162
0.8494	Intermediate Similarity	NPC83922
0.8494	Intermediate Similarity	NPC472448
0.8494	Intermediate Similarity	NPC329760
0.8494	Intermediate Similarity	NPC474150
0.8491	Intermediate Similarity	NPC472918
0.8491	Intermediate Similarity	NPC308200
0.8488	Intermediate Similarity	NPC77179
0.8488	Intermediate Similarity	NPC23553
0.8488	Intermediate Similarity	NPC246877
0.8485	Intermediate Similarity	NPC243701
0.8485	Intermediate Similarity	NPC471976
0.8485	Intermediate Similarity	NPC470810
0.8481	Intermediate Similarity	NPC311144
0.8481	Intermediate Similarity	NPC212697
0.8481	Intermediate Similarity	NPC303185
0.8481	Intermediate Similarity	NPC184649
0.848	Intermediate Similarity	NPC232412
0.848	Intermediate Similarity	NPC86809
0.848	Intermediate Similarity	NPC98667
0.848	Intermediate Similarity	NPC289244
0.8476	Intermediate Similarity	NPC129684
0.8476	Intermediate Similarity	NPC165977
0.8476	Intermediate Similarity	NPC299520
0.8476	Intermediate Similarity	NPC196448
0.8476	Intermediate Similarity	NPC217677
0.8476	Intermediate Similarity	NPC67876
0.8476	Intermediate Similarity	NPC476981
0.8476	Intermediate Similarity	NPC65504
0.8471	Intermediate Similarity	NPC472620
0.8471	Intermediate Similarity	NPC223375
0.8471	Intermediate Similarity	NPC204469
0.8471	Intermediate Similarity	NPC475825
0.8466	Intermediate Similarity	NPC48579
0.8466	Intermediate Similarity	NPC32557
0.8466	Intermediate Similarity	NPC472909
0.8466	Intermediate Similarity	NPC189960
0.8466	Intermediate Similarity	NPC259710
0.8466	Intermediate Similarity	NPC207809
0.8466	Intermediate Similarity	NPC471456
0.8466	Intermediate Similarity	NPC304207
0.8466	Intermediate Similarity	NPC234485

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 NPC476931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	903
0.2-0.3	1714
0.3-0.4	2659
0.4-0.5	1991
0.5-0.6	1010
0.6-0.7	348
0.7-0.8	152
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
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8373	Intermediate Similarity	NPD5494	Approved
0.8365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1934	Approved
0.811	Intermediate Similarity	NPD4380	Phase 2
0.8107	Intermediate Similarity	NPD1247	Approved
0.807	Intermediate Similarity	NPD6166	Phase 2
0.807	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7411	Suspended
0.805	Intermediate Similarity	NPD2800	Approved
0.8036	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1549	Phase 2
0.7978	Intermediate Similarity	NPD8434	Phase 2
0.7975	Intermediate Similarity	NPD1512	Approved
0.7965	Intermediate Similarity	NPD2403	Approved
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD6799	Approved
0.7931	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7473	Discontinued
0.7917	Intermediate Similarity	NPD3817	Phase 2
0.7917	Intermediate Similarity	NPD5402	Approved
0.7914	Intermediate Similarity	NPD2534	Approved
0.7914	Intermediate Similarity	NPD2533	Approved
0.7914	Intermediate Similarity	NPD2532	Approved
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7874	Intermediate Similarity	NPD3818	Discontinued
0.7874	Intermediate Similarity	NPD3751	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1511	Approved
0.7853	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6232	Discontinued
0.7841	Intermediate Similarity	NPD6797	Phase 2
0.7829	Intermediate Similarity	NPD5844	Phase 1
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1510	Phase 2
0.7797	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD1240	Approved
0.7765	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7808	Phase 3
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD2796	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7725	Intermediate Similarity	NPD3226	Approved
0.7711	Intermediate Similarity	NPD5403	Approved
0.7702	Intermediate Similarity	NPD1471	Phase 3
0.7701	Intermediate Similarity	NPD3926	Phase 2
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7684	Intermediate Similarity	NPD7074	Phase 3
0.768	Intermediate Similarity	NPD8150	Discontinued
0.7674	Intermediate Similarity	NPD919	Approved
0.7644	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD7054	Approved
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5401	Approved
0.7584	Intermediate Similarity	NPD7472	Approved
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7544	Intermediate Similarity	NPD1465	Phase 2
0.7542	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD6651	Approved
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6782	Approved
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7394	Intermediate Similarity	NPD1243	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3300	Phase 2
0.7363	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2799	Discontinued
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8312	Approved
0.7322	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4749	Approved
0.7306	Intermediate Similarity	NPD7697	Approved
0.7306	Intermediate Similarity	NPD7698	Approved
0.7306	Intermediate Similarity	NPD7696	Phase 3
0.7305	Intermediate Similarity	NPD2309	Approved
0.7303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD447	Suspended
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD7907	Approved
0.7228	Intermediate Similarity	NPD4665	Approved
0.7228	Intermediate Similarity	NPD4111	Phase 1
0.7222	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD7390	Discontinued
0.7213	Intermediate Similarity	NPD6765	Approved
0.7213	Intermediate Similarity	NPD6764	Approved
0.7205	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7193	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7184	Intermediate Similarity	NPD37	Approved
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6234	Discontinued
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4965	Approved
0.7159	Intermediate Similarity	NPD4967	Phase 2
0.7159	Intermediate Similarity	NPD4966	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7136	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD4287	Approved
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7199	Phase 2
0.7088	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD230	Phase 1
0.7068	Intermediate Similarity	NPD4363	Phase 3
0.7068	Intermediate Similarity	NPD4360	Phase 2
0.7063	Intermediate Similarity	NPD2798	Approved
0.7059	Intermediate Similarity	NPD6785	Approved
0.7059	Intermediate Similarity	NPD6784	Approved
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7025	Intermediate Similarity	NPD9717	Approved
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD1470	Approved
0.6994	Remote Similarity	NPD3764	Approved
0.699	Remote Similarity	NPD3057	Approved
0.699	Remote Similarity	NPD6823	Phase 2
0.6982	Remote Similarity	NPD2654	Approved
0.6975	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1933	Approved
0.697	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD5124	Phase 1
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1610	Phase 2
0.6962	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8151	Discontinued
0.6946	Remote Similarity	NPD7033	Discontinued
0.6946	Remote Similarity	NPD4308	Phase 3
0.6946	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4361	Phase 2
0.6943	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3446	Phase 1
0.6939	Remote Similarity	NPD2493	Approved
0.6939	Remote Similarity	NPD2494	Approved
0.6923	Remote Similarity	NPD2424	Discontinued
0.6919	Remote Similarity	NPD4583	Approved
0.6919	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4582	Approved
0.6914	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4060	Phase 1
0.6909	Remote Similarity	NPD1613	Approved
0.6907	Remote Similarity	NPD2974	Approved
0.6907	Remote Similarity	NPD2975	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