NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	556.14
Volume:	544.385
LogP:	4.323
LogD:	2.987
LogS:	-6.035
# Rotatable Bonds:	4
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	4.103
Fsp3:	0.161
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.104
MDCK Permeability:	7.292956070159562e-06
Pgp-inhibitor:	0.384
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.443
20% Bioavailability (F20%):	0.153
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.28377532958984%
Volume Distribution (VD):	0.484
Pgp-substrate:	2.1015641689300537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.364
CYP1A2-substrate:	0.315
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.339
CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	5.712
Half-life (T1/2):	0.317

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.572
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.156
Skin Sensitization:	0.897
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.87
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC61112

Natural Product ID:	NPC61112
*Common Name:**	Sikokianin B
IUPAC Name:	(2R,3R)-3-[(2R,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	QOPUSVUZHPIYER-JHYZPVKISA-N
Standard InCHI:	InChI=1S/C31H24O10/c1-39-19-8-4-15(5-9-19)31-27(29(38)25-21(36)11-18(34)13-23(25)41-31)26-28(37)24-20(35)10-17(33)12-22(24)40-30(26)14-2-6-16(32)7-3-14/h2-13,26-27,30-36H,1H3/t26-,27+,30-,31-/m0/s1
SMILES:	COC1=CC=C(C=C1)[C@H]2[C@@H](C(=O)C3=C(C=C(C=C3O2)O)O)[C@@H]4[C@@H](OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49798955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15635251]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[24660446]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[501363]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320737]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3837	Wikstroemia indica	Species	Thymelaeaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.54	ug/ml	PMID[19299148]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.54	ug/ml	PMID[22269277]

☑ 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 NPC61112 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	401
0.1-0.2	1611
0.2-0.3	3708
0.3-0.4	9253
0.4-0.5	9402
0.5-0.6	3681
0.6-0.7	5810
0.7-0.8	5086
0.8-0.85	2654
0.85-0.9	902
0.9-0.95	172
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC198489
0.9933	High Similarity	NPC287789
0.9933	High Similarity	NPC271741
0.9932	High Similarity	NPC258474
0.9932	High Similarity	NPC201227
0.9866	High Similarity	NPC309648
0.9733	High Similarity	NPC69531
0.9669	High Similarity	NPC475184
0.9603	High Similarity	NPC32867
0.9539	High Similarity	NPC1796
0.9536	High Similarity	NPC134171
0.9536	High Similarity	NPC300668
0.9477	High Similarity	NPC51760
0.9477	High Similarity	NPC51247
0.9477	High Similarity	NPC295090
0.9416	High Similarity	NPC42965
0.9416	High Similarity	NPC226462
0.9416	High Similarity	NPC98023
0.9412	High Similarity	NPC257166
0.9408	High Similarity	NPC182555
0.9408	High Similarity	NPC66441
0.9404	High Similarity	NPC174086
0.9359	High Similarity	NPC63438
0.9355	High Similarity	NPC301256
0.9355	High Similarity	NPC312273
0.9351	High Similarity	NPC105584
0.9351	High Similarity	NPC15815
0.9342	High Similarity	NPC121568
0.9333	High Similarity	NPC3642
0.9324	High Similarity	NPC311144
0.9299	High Similarity	NPC473010
0.9295	High Similarity	NPC473012
0.929	High Similarity	NPC195136
0.9281	High Similarity	NPC37253
0.9281	High Similarity	NPC79375
0.9267	High Similarity	NPC122894
0.9262	High Similarity	NPC299011
0.9257	High Similarity	NPC113770
0.9241	High Similarity	NPC224851
0.9236	High Similarity	NPC38591
0.9236	High Similarity	NPC473009
0.9216	High Similarity	NPC303485
0.9216	High Similarity	NPC71061
0.9216	High Similarity	NPC194593
0.9216	High Similarity	NPC72425
0.9216	High Similarity	NPC290830
0.9211	High Similarity	NPC178484
0.9205	High Similarity	NPC473016
0.92	High Similarity	NPC308200
0.9195	High Similarity	NPC184649
0.9195	High Similarity	NPC303185
0.9172	High Similarity	NPC15374
0.9172	High Similarity	NPC473011
0.9167	High Similarity	NPC121647
0.9161	High Similarity	NPC324358
0.9161	High Similarity	NPC323627
0.9161	High Similarity	NPC208258
0.9161	High Similarity	NPC318527
0.9161	High Similarity	NPC322459
0.9156	High Similarity	NPC215203
0.9156	High Similarity	NPC186227
0.9156	High Similarity	NPC159707
0.9156	High Similarity	NPC150908
0.9156	High Similarity	NPC14606
0.9156	High Similarity	NPC52611
0.9156	High Similarity	NPC158027
0.9156	High Similarity	NPC100049
0.9156	High Similarity	NPC205026
0.9156	High Similarity	NPC265624
0.9156	High Similarity	NPC121649
0.9156	High Similarity	NPC248739
0.915	High Similarity	NPC78324
0.915	High Similarity	NPC39154
0.915	High Similarity	NPC115601
0.915	High Similarity	NPC208011
0.9145	High Similarity	NPC29777
0.9145	High Similarity	NPC471115
0.9139	High Similarity	NPC39195
0.9139	High Similarity	NPC145467
0.9133	High Similarity	NPC470133
0.9133	High Similarity	NPC470132
0.9133	High Similarity	NPC228779
0.9133	High Similarity	NPC473078
0.9133	High Similarity	NPC470131
0.9133	High Similarity	NPC470134
0.9133	High Similarity	NPC109183
0.9119	High Similarity	NPC171985
0.9119	High Similarity	NPC251336
0.9119	High Similarity	NPC320741
0.9108	High Similarity	NPC18380
0.9103	High Similarity	NPC123544
0.9085	High Similarity	NPC222713
0.9085	High Similarity	NPC111112
0.9085	High Similarity	NPC148945
0.9085	High Similarity	NPC309512
0.9085	High Similarity	NPC78835
0.9085	High Similarity	NPC204561
0.9085	High Similarity	NPC138299
0.9085	High Similarity	NPC317715
0.9085	High Similarity	NPC316960
0.9085	High Similarity	NPC67322
0.9079	High Similarity	NPC288840
0.9079	High Similarity	NPC291746
0.9079	High Similarity	NPC471114
0.9067	High Similarity	NPC271288
0.9067	High Similarity	NPC470135
0.9067	High Similarity	NPC470136
0.9067	High Similarity	NPC39045
0.906	High Similarity	NPC202981
0.9057	High Similarity	NPC477840
0.9054	High Similarity	NPC284550
0.9054	High Similarity	NPC110228
0.9054	High Similarity	NPC76445
0.9054	High Similarity	NPC6407
0.9054	High Similarity	NPC129853
0.9054	High Similarity	NPC188243
0.9051	High Similarity	NPC477841
0.9045	High Similarity	NPC184326
0.9045	High Similarity	NPC292863
0.9026	High Similarity	NPC43345
0.9013	High Similarity	NPC35150
0.9013	High Similarity	NPC106328
0.9012	High Similarity	NPC186847
0.9012	High Similarity	NPC472454
0.9012	High Similarity	NPC257667
0.9007	High Similarity	NPC472629
0.9006	High Similarity	NPC53252
0.9006	High Similarity	NPC107627
0.9	High Similarity	NPC85162
0.9	High Similarity	NPC223812
0.9	High Similarity	NPC77794
0.9	High Similarity	NPC82330
0.9	High Similarity	NPC278249
0.9	High Similarity	NPC107177
0.9	High Similarity	NPC81697
0.9	High Similarity	NPC125894
0.8987	High Similarity	NPC137232
0.8986	High Similarity	NPC140890
0.8986	High Similarity	NPC329203
0.8986	High Similarity	NPC274784
0.8986	High Similarity	NPC150648
0.8986	High Similarity	NPC222342
0.8986	High Similarity	NPC225153
0.8986	High Similarity	NPC310135
0.8986	High Similarity	NPC20709
0.8986	High Similarity	NPC316480
0.8986	High Similarity	NPC265871
0.8981	High Similarity	NPC195167
0.8974	High Similarity	NPC54830
0.8974	High Similarity	NPC56049
0.8968	High Similarity	NPC326592
0.8968	High Similarity	NPC324447
0.8968	High Similarity	NPC112701
0.8968	High Similarity	NPC203080
0.8968	High Similarity	NPC109594
0.8961	High Similarity	NPC312549
0.8961	High Similarity	NPC476551
0.8961	High Similarity	NPC476553
0.8961	High Similarity	NPC476552
0.8961	High Similarity	NPC209142
0.8957	High Similarity	NPC168789
0.8954	High Similarity	NPC132345
0.8951	High Similarity	NPC287884
0.8951	High Similarity	NPC8704
0.8947	High Similarity	NPC261271
0.8947	High Similarity	NPC296998
0.8947	High Similarity	NPC10990
0.8947	High Similarity	NPC473077
0.8947	High Similarity	NPC475348
0.8947	High Similarity	NPC300988
0.894	High Similarity	NPC87486
0.894	High Similarity	NPC470890
0.894	High Similarity	NPC235217
0.894	High Similarity	NPC131579
0.894	High Similarity	NPC473015
0.894	High Similarity	NPC131568
0.894	High Similarity	NPC473013
0.894	High Similarity	NPC473014
0.894	High Similarity	NPC124780
0.8933	High Similarity	NPC167624
0.8933	High Similarity	NPC107572
0.8933	High Similarity	NPC194432
0.8933	High Similarity	NPC66515
0.8933	High Similarity	NPC177354
0.8933	High Similarity	NPC1089
0.8933	High Similarity	NPC32739
0.8933	High Similarity	NPC166934
0.8933	High Similarity	NPC296917
0.8933	High Similarity	NPC228504
0.8933	High Similarity	NPC182852
0.8933	High Similarity	NPC64915
0.8933	High Similarity	NPC265040
0.8933	High Similarity	NPC328164
0.8933	High Similarity	NPC40833
0.8933	High Similarity	NPC148757
0.8933	High Similarity	NPC76372
0.8933	High Similarity	NPC10937
0.8933	High Similarity	NPC161506
0.8933	High Similarity	NPC324134
0.8933	High Similarity	NPC76338

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 NPC61112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	948
0.2-0.3	1559
0.3-0.4	2637
0.4-0.5	1917
0.5-0.6	1133
0.6-0.7	387
0.7-0.8	150
0.8-0.85	41
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9156	High Similarity	NPD8443	Clinical (unspecified phase)
0.9108	High Similarity	NPD6959	Discontinued
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD7852	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8792	High Similarity	NPD1549	Phase 2
0.8718	High Similarity	NPD7411	Suspended
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8693	High Similarity	NPD7410	Clinical (unspecified phase)
0.8654	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8544	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD2796	Approved
0.85	High Similarity	NPD7768	Phase 2
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD3749	Approved
0.8434	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7074	Phase 3
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7054	Approved
0.8322	Intermediate Similarity	NPD1240	Approved
0.8274	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD1607	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD4908	Phase 1
0.8153	Intermediate Similarity	NPD1511	Approved
0.8133	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD7808	Phase 3
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8077	Intermediate Similarity	NPD3750	Approved
0.8067	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1512	Approved
0.8049	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD3818	Discontinued
0.8038	Intermediate Similarity	NPD7390	Discontinued
0.8038	Intermediate Similarity	NPD6799	Approved
0.8013	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2344	Approved
0.7988	Intermediate Similarity	NPD3817	Phase 2
0.7977	Intermediate Similarity	NPD8313	Approved
0.7977	Intermediate Similarity	NPD8312	Approved
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD5403	Approved
0.7879	Intermediate Similarity	NPD5402	Approved
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7803	Intermediate Similarity	NPD5953	Discontinued
0.7799	Intermediate Similarity	NPD2309	Approved
0.7791	Intermediate Similarity	NPD3226	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD5401	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7756	Intermediate Similarity	NPD3748	Approved
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD1465	Phase 2
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7703	Intermediate Similarity	NPD1610	Phase 2
0.768	Intermediate Similarity	NPD4363	Phase 3
0.768	Intermediate Similarity	NPD4360	Phase 2
0.7669	Intermediate Similarity	NPD920	Approved
0.7661	Intermediate Similarity	NPD3926	Phase 2
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.7595	Intermediate Similarity	NPD2935	Discontinued
0.7586	Intermediate Similarity	NPD7286	Phase 2
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD3268	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.747	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7459	Intermediate Similarity	NPD4287	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7451	Intermediate Similarity	NPD2798	Approved
0.7447	Intermediate Similarity	NPD7697	Approved
0.7447	Intermediate Similarity	NPD7696	Phase 3
0.7447	Intermediate Similarity	NPD7698	Approved
0.7438	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7407	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD7003	Approved
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7870	Phase 2
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD943	Approved
0.7386	Intermediate Similarity	NPD1203	Approved
0.7386	Intermediate Similarity	NPD2797	Approved
0.7358	Intermediate Similarity	NPD7097	Phase 1
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7349	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7341	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7228	Approved
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7292	Intermediate Similarity	NPD7701	Phase 2
0.729	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD7213	Phase 3
0.7273	Intermediate Similarity	NPD7212	Phase 2
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7267	Intermediate Similarity	NPD5405	Approved
0.7267	Intermediate Similarity	NPD5406	Approved
0.7267	Intermediate Similarity	NPD5404	Approved
0.7267	Intermediate Similarity	NPD5408	Approved
0.7261	Intermediate Similarity	NPD3764	Approved
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7258	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4361	Phase 2
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD2296	Approved
0.7241	Intermediate Similarity	NPD1247	Approved
0.7235	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD7577	Discontinued
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7229	Intermediate Similarity	NPD7447	Phase 1
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD4965	Approved
0.7204	Intermediate Similarity	NPD6534	Approved
0.7204	Intermediate Similarity	NPD6535	Approved
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5760	Phase 2
0.7193	Intermediate Similarity	NPD5761	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7186	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD7700	Phase 2
0.7181	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD7801	Approved
0.7161	Intermediate Similarity	NPD3266	Approved
0.7161	Intermediate Similarity	NPD3267	Approved
0.7161	Intermediate Similarity	NPD1470	Approved
0.7151	Intermediate Similarity	NPD4288	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD6279	Approved
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7135	Intermediate Similarity	NPD8319	Approved
0.7135	Intermediate Similarity	NPD6280	Approved
0.7135	Intermediate Similarity	NPD8320	Phase 1
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2654	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD919	Approved
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD1899	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