NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	378.15
Volume:	392.361
LogP:	6.052
LogD:	3.603
LogS:	-2.818
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	3.201
Fsp3:	0.261
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:	-4.779
MDCK Permeability:	1.685535789874848e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.138
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	93.08455657958984%
Volume Distribution (VD):	0.656
Pgp-substrate:	8.517876625061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.816
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.861
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.305
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	2.22
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.579
Rat Oral Acute Toxicity:	0.624
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.742
Carcinogencity:	0.861
Eye Corrosion:	0.003
Eye Irritation:	0.192
Respiratory Toxicity:	0.676

Download Data

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

Natural Product: NPC280530

Natural Product ID:	NPC280530
*Common Name:**	9,11-Dihydroxy-3,3-dimethyl-10-(3-methyl-but-2-enyl)-3H-pyrano(3,2-a)xanthen-12-one
IUPAC Name:	9,11-dihydroxy-3,3-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-a]xanthen-12-one
Synonyms:	Calothwaitesixanthone
Standard InCHIKey:	HPCMZEMPMMZZPL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O5/c1-12(2)5-6-13-15(24)11-18-20(21(13)25)22(26)19-14-9-10-23(3,4)28-16(14)7-8-17(19)27-18/h5,7-11,24-25H,6H2,1-4H3
SMILES:	CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C4=C(C=C3)OC(C=C4)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5495848
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 [CHEMONTID:0003517] 2-prenylated 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
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2737	Calophyllum caledonicum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.7	ug/ml	PMID[19299148]

☑ 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 NPC280530 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	452
0.1-0.2	1789
0.2-0.3	4162
0.3-0.4	10627
0.4-0.5	7585
0.5-0.6	3734
0.6-0.7	5509
0.7-0.8	4599
0.8-0.85	2317
0.85-0.9	1591
0.9-0.95	317
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC178964
1.0	High Similarity	NPC95842
0.9797	High Similarity	NPC166054
0.9797	High Similarity	NPC55662
0.9795	High Similarity	NPC227122
0.966	High Similarity	NPC101957
0.966	High Similarity	NPC120105
0.9592	High Similarity	NPC65775
0.9592	High Similarity	NPC10027
0.9542	High Similarity	NPC229632
0.9542	High Similarity	NPC329760
0.9524	High Similarity	NPC186397
0.9524	High Similarity	NPC37135
0.9481	High Similarity	NPC189473
0.9481	High Similarity	NPC23298
0.9481	High Similarity	NPC207690
0.9459	High Similarity	NPC223988
0.9459	High Similarity	NPC266499
0.9419	High Similarity	NPC472450
0.9419	High Similarity	NPC275780
0.9419	High Similarity	NPC239752
0.9416	High Similarity	NPC472402
0.94	High Similarity	NPC474843
0.9396	High Similarity	NPC472633
0.9396	High Similarity	NPC471115
0.9396	High Similarity	NPC29777
0.9384	High Similarity	NPC219915
0.9359	High Similarity	NPC37870
0.9359	High Similarity	NPC39091
0.9359	High Similarity	NPC472449
0.9342	High Similarity	NPC142339
0.9338	High Similarity	NPC135522
0.9338	High Similarity	NPC329844
0.9329	High Similarity	NPC473978
0.929	High Similarity	NPC25152
0.9286	High Similarity	NPC80375
0.9286	High Similarity	NPC235018
0.9286	High Similarity	NPC204290
0.9286	High Similarity	NPC45146
0.9286	High Similarity	NPC139036
0.9286	High Similarity	NPC471973
0.9281	High Similarity	NPC268360
0.9281	High Similarity	NPC165977
0.9281	High Similarity	NPC217677
0.9281	High Similarity	NPC44199
0.9281	High Similarity	NPC236796
0.9272	High Similarity	NPC142527
0.9267	High Similarity	NPC37348
0.9262	High Similarity	NPC296869
0.9252	High Similarity	NPC38219
0.9231	High Similarity	NPC236521
0.9231	High Similarity	NPC248638
0.9231	High Similarity	NPC152659
0.9226	High Similarity	NPC32694
0.9226	High Similarity	NPC474187
0.9226	High Similarity	NPC61010
0.9226	High Similarity	NPC167678
0.9226	High Similarity	NPC29876
0.9221	High Similarity	NPC100123
0.9221	High Similarity	NPC474290
0.9221	High Similarity	NPC186113
0.9216	High Similarity	NPC276444
0.9211	High Similarity	NPC210942
0.9211	High Similarity	NPC89474
0.9211	High Similarity	NPC169990
0.9205	High Similarity	NPC305965
0.92	High Similarity	NPC288036
0.92	High Similarity	NPC97029
0.92	High Similarity	NPC97028
0.92	High Similarity	NPC65589
0.92	High Similarity	NPC158338
0.92	High Similarity	NPC100985
0.9195	High Similarity	NPC14001
0.9195	High Similarity	NPC296998
0.9195	High Similarity	NPC166757
0.9195	High Similarity	NPC473077
0.9195	High Similarity	NPC308200
0.9189	High Similarity	NPC311741
0.9189	High Similarity	NPC234629
0.9184	High Similarity	NPC299080
0.9184	High Similarity	NPC144499
0.9184	High Similarity	NPC59739
0.9184	High Similarity	NPC159855
0.9184	High Similarity	NPC217083
0.9184	High Similarity	NPC78803
0.9184	High Similarity	NPC62840
0.9184	High Similarity	NPC214236
0.9184	High Similarity	NPC310340
0.9184	High Similarity	NPC293852
0.9184	High Similarity	NPC169479
0.9178	High Similarity	NPC275734
0.9177	High Similarity	NPC225419
0.9172	High Similarity	NPC156432
0.9167	High Similarity	NPC83922
0.9167	High Similarity	NPC472448
0.9167	High Similarity	NPC473961
0.9167	High Similarity	NPC52204
0.9161	High Similarity	NPC228785
0.9161	High Similarity	NPC471976
0.9161	High Similarity	NPC320359
0.9161	High Similarity	NPC475886
0.9161	High Similarity	NPC56085
0.9161	High Similarity	NPC119224
0.9161	High Similarity	NPC200746
0.9161	High Similarity	NPC474287
0.9161	High Similarity	NPC14353
0.9156	High Similarity	NPC218871
0.9156	High Similarity	NPC476981
0.9156	High Similarity	NPC476630
0.9156	High Similarity	NPC196448
0.9156	High Similarity	NPC136674
0.915	High Similarity	NPC275575
0.915	High Similarity	NPC476169
0.915	High Similarity	NPC99199
0.9145	High Similarity	NPC217447
0.9145	High Similarity	NPC45934
0.9139	High Similarity	NPC202595
0.9139	High Similarity	NPC471984
0.9133	High Similarity	NPC27221
0.9133	High Similarity	NPC256672
0.9133	High Similarity	NPC7025
0.9133	High Similarity	NPC145467
0.9133	High Similarity	NPC244407
0.9133	High Similarity	NPC266572
0.9133	High Similarity	NPC39195
0.9128	High Similarity	NPC214774
0.9128	High Similarity	NPC290133
0.9128	High Similarity	NPC220418
0.9128	High Similarity	NPC473135
0.9128	High Similarity	NPC20488
0.9128	High Similarity	NPC187282
0.9128	High Similarity	NPC24136
0.9128	High Similarity	NPC301276
0.9128	High Similarity	NPC312973
0.9128	High Similarity	NPC475052
0.9128	High Similarity	NPC267375
0.9128	High Similarity	NPC54577
0.9128	High Similarity	NPC473132
0.9128	High Similarity	NPC246948
0.9128	High Similarity	NPC142405
0.9128	High Similarity	NPC470647
0.9128	High Similarity	NPC83357
0.9128	High Similarity	NPC67805
0.9128	High Similarity	NPC176229
0.9128	High Similarity	NPC470676
0.9128	High Similarity	NPC88964
0.9128	High Similarity	NPC124729
0.9128	High Similarity	NPC195621
0.9128	High Similarity	NPC111786
0.9128	High Similarity	NPC477955
0.9122	High Similarity	NPC212932
0.9122	High Similarity	NPC166138
0.9122	High Similarity	NPC18585
0.9122	High Similarity	NPC190637
0.9122	High Similarity	NPC106985
0.9122	High Similarity	NPC24821
0.9122	High Similarity	NPC11700
0.9122	High Similarity	NPC9117
0.9122	High Similarity	NPC293053
0.9116	High Similarity	NPC147688
0.9116	High Similarity	NPC156590
0.9116	High Similarity	NPC64908
0.9116	High Similarity	NPC118840
0.9116	High Similarity	NPC205006
0.9114	High Similarity	NPC120593
0.911	High Similarity	NPC96565
0.911	High Similarity	NPC301217
0.911	High Similarity	NPC220062
0.911	High Similarity	NPC303633
0.911	High Similarity	NPC216978
0.911	High Similarity	NPC55018
0.9108	High Similarity	NPC186686
0.9108	High Similarity	NPC220313
0.9108	High Similarity	NPC146134
0.9108	High Similarity	NPC306321
0.9108	High Similarity	NPC303460
0.9103	High Similarity	NPC278052
0.9103	High Similarity	NPC3629
0.9103	High Similarity	NPC475883
0.9103	High Similarity	NPC278427
0.9103	High Similarity	NPC259456
0.9103	High Similarity	NPC474186
0.9103	High Similarity	NPC474351
0.9103	High Similarity	NPC66288
0.9103	High Similarity	NPC40491
0.9097	High Similarity	NPC476242
0.9097	High Similarity	NPC185258
0.9097	High Similarity	NPC172770
0.9091	High Similarity	NPC274730
0.9091	High Similarity	NPC68093
0.9091	High Similarity	NPC191146
0.9085	High Similarity	NPC170492
0.9085	High Similarity	NPC472462
0.9085	High Similarity	NPC214632
0.9085	High Similarity	NPC235333
0.9079	High Similarity	NPC202157
0.9079	High Similarity	NPC474417
0.9079	High Similarity	NPC72958
0.9079	High Similarity	NPC258249
0.9079	High Similarity	NPC232645

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 NPC280530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	994
0.2-0.3	1559
0.3-0.4	2687
0.4-0.5	1931
0.5-0.6	1004
0.6-0.7	376
0.7-0.8	135
0.8-0.85	46
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD4378	Clinical (unspecified phase)
0.8933	High Similarity	NPD7410	Clinical (unspecified phase)
0.8839	High Similarity	NPD2801	Approved
0.8839	High Similarity	NPD7819	Suspended
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD6959	Discontinued
0.8662	High Similarity	NPD8443	Clinical (unspecified phase)
0.8645	High Similarity	NPD4380	Phase 2
0.8618	High Similarity	NPD1511	Approved
0.8591	High Similarity	NPD1552	Clinical (unspecified phase)
0.8591	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD5494	Approved
0.8553	High Similarity	NPD3749	Approved
0.8543	High Similarity	NPD3750	Approved
0.8535	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD1549	Phase 2
0.8506	High Similarity	NPD1512	Approved
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8411	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2796	Approved
0.8355	Intermediate Similarity	NPD2800	Approved
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2533	Approved
0.8323	Intermediate Similarity	NPD2534	Approved
0.8323	Intermediate Similarity	NPD2532	Approved
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8311	Intermediate Similarity	NPD1240	Approved
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8278	Intermediate Similarity	NPD2935	Discontinued
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3226	Approved
0.8224	Intermediate Similarity	NPD2346	Discontinued
0.8212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD3748	Approved
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1607	Approved
0.8158	Intermediate Similarity	NPD6099	Approved
0.8158	Intermediate Similarity	NPD6100	Approved
0.8148	Intermediate Similarity	NPD7768	Phase 2
0.8148	Intermediate Similarity	NPD3882	Suspended
0.8141	Intermediate Similarity	NPD7390	Discontinued
0.8118	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7054	Approved
0.8086	Intermediate Similarity	NPD5402	Approved
0.8086	Intermediate Similarity	NPD3817	Phase 2
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8047	Intermediate Similarity	NPD7472	Approved
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD4625	Phase 3
0.7974	Intermediate Similarity	NPD2799	Discontinued
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7251	Discontinued
0.7933	Intermediate Similarity	NPD2313	Discontinued
0.7911	Intermediate Similarity	NPD6799	Approved
0.7907	Intermediate Similarity	NPD7808	Phase 3
0.7885	Intermediate Similarity	NPD1243	Approved
0.7885	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD920	Approved
0.7871	Intermediate Similarity	NPD2344	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7844	Intermediate Similarity	NPD1247	Approved
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7834	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5710	Approved
0.7798	Intermediate Similarity	NPD5711	Approved
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6651	Approved
0.7719	Intermediate Similarity	NPD3751	Discontinued
0.7712	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7682	Intermediate Similarity	NPD4908	Phase 1
0.7674	Intermediate Similarity	NPD7286	Phase 2
0.7673	Intermediate Similarity	NPD2309	Approved
0.7667	Intermediate Similarity	NPD4360	Phase 2
0.7667	Intermediate Similarity	NPD4363	Phase 3
0.7654	Intermediate Similarity	NPD5403	Approved
0.765	Intermediate Similarity	NPD6782	Approved
0.765	Intermediate Similarity	NPD6776	Approved
0.765	Intermediate Similarity	NPD6778	Approved
0.765	Intermediate Similarity	NPD6781	Approved
0.765	Intermediate Similarity	NPD6779	Approved
0.765	Intermediate Similarity	NPD6780	Approved
0.765	Intermediate Similarity	NPD6777	Approved
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1470	Approved
0.7588	Intermediate Similarity	NPD7229	Phase 3
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3268	Approved
0.758	Intermediate Similarity	NPD5406	Approved
0.758	Intermediate Similarity	NPD5408	Approved
0.758	Intermediate Similarity	NPD5405	Approved
0.758	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD1201	Approved
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8312	Approved
0.7557	Intermediate Similarity	NPD8313	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2798	Approved
0.7545	Intermediate Similarity	NPD4288	Approved
0.7544	Intermediate Similarity	NPD3926	Phase 2
0.7542	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4287	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD6844	Discontinued
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7698	Approved
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD919	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7483	Intermediate Similarity	NPD2797	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD3764	Approved
0.7467	Intermediate Similarity	NPD4749	Approved
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7783	Phase 2
0.743	Intermediate Similarity	NPD8150	Discontinued
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1471	Phase 3
0.7405	Intermediate Similarity	NPD4308	Phase 3
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.74	Intermediate Similarity	NPD1608	Approved
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.738	Intermediate Similarity	NPD6823	Phase 2
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4361	Phase 2
0.7337	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD447	Suspended
0.7303	Intermediate Similarity	NPD3225	Approved
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7699	Phase 2
0.7258	Intermediate Similarity	NPD7700	Phase 2
0.7255	Intermediate Similarity	NPD3267	Approved
0.7255	Intermediate Similarity	NPD3266	Approved
0.7254	Intermediate Similarity	NPD7801	Approved
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7229	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD230	Phase 1
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6671	Approved
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6585	Discontinued
0.72	Intermediate Similarity	NPD17	Approved
0.7195	Intermediate Similarity	NPD3300	Phase 2
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.719	Intermediate Similarity	NPD6696	Suspended
0.7176	Intermediate Similarity	NPD5761	Phase 2
0.7176	Intermediate Similarity	NPD5760	Phase 2
0.7169	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)

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