NPASS Compound

Structure

NPC471291 OpenBabel07101718292D 23 26 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 11 2 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 12 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.06
Volume:	300.012
LogP:	2.31
LogD:	2.196
LogS:	-3.731
# Rotatable Bonds:	1
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.341
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.927
MDCK Permeability:	8.171683475666214e-06
Pgp-inhibitor:	0.029
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.817

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	95.14728546142578%
Volume Distribution (VD):	0.623
Pgp-substrate:	3.9287831783294678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.868
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.658
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	1.323
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.353
Skin Sensitization:	0.498
Carcinogencity:	0.801
Eye Corrosion:	0.015
Eye Irritation:	0.894
Respiratory Toxicity:	0.548

Download Data

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

Natural Product: NPC471291

Natural Product ID:	NPC471291
*Common Name:**	Rac-Boeravinone K
IUPAC Name:	9,11-dihydroxy-6-methoxy-6H-chromeno[3,4-b]chromen-12-one
Synonyms:
Standard InCHIKey:	FEMUUAWKOBNFCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12O6/c1-21-17-16-13(9-4-2-3-5-11(9)23-17)15(20)14-10(19)6-8(18)7-12(14)22-16/h2-7,17-19H,1H3
SMILES:	COC1C2=C(C3=CC=CC=C3O1)C(=O)C4=C(C=C(C=C4O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408968
PubChem CID:	72190428
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	44.6	%	PMID[494381]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	59.4	%	PMID[494381]

☑ 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 NPC471291 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	418
0.1-0.2	1846
0.2-0.3	4284
0.3-0.4	9979
0.4-0.5	8236
0.5-0.6	4045
0.6-0.7	5859
0.7-0.8	4168
0.8-0.85	2598
0.85-0.9	1185
0.9-0.95	72
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC168805
0.9863	High Similarity	NPC121910
0.9726	High Similarity	NPC470771
0.9726	High Similarity	NPC471289
0.9662	High Similarity	NPC87404
0.9662	High Similarity	NPC92395
0.9474	High Similarity	NPC470756
0.9346	High Similarity	NPC471290
0.9342	High Similarity	NPC73511
0.929	High Similarity	NPC470773
0.9276	High Similarity	NPC161749
0.9276	High Similarity	NPC258035
0.9276	High Similarity	NPC197896
0.9276	High Similarity	NPC156457
0.9276	High Similarity	NPC313163
0.9272	High Similarity	NPC95090
0.9272	High Similarity	NPC27408
0.9226	High Similarity	NPC470772
0.9221	High Similarity	NPC303913
0.9211	High Similarity	NPC45165
0.9211	High Similarity	NPC206378
0.9205	High Similarity	NPC83283
0.9205	High Similarity	NPC143851
0.9205	High Similarity	NPC39360
0.9205	High Similarity	NPC210003
0.9205	High Similarity	NPC106625
0.9205	High Similarity	NPC29763
0.9161	High Similarity	NPC44947
0.9161	High Similarity	NPC131745
0.915	High Similarity	NPC6985
0.915	High Similarity	NPC60966
0.915	High Similarity	NPC44931
0.915	High Similarity	NPC129827
0.915	High Similarity	NPC65003
0.915	High Similarity	NPC473512
0.915	High Similarity	NPC108831
0.915	High Similarity	NPC182634
0.9145	High Similarity	NPC99233
0.9145	High Similarity	NPC26195
0.9145	High Similarity	NPC97052
0.9145	High Similarity	NPC169248
0.9145	High Similarity	NPC72649
0.9145	High Similarity	NPC39351
0.9139	High Similarity	NPC121001
0.9139	High Similarity	NPC259182
0.9128	High Similarity	NPC266572
0.9114	High Similarity	NPC471287
0.9103	High Similarity	NPC66087
0.9103	High Similarity	NPC278419
0.9103	High Similarity	NPC179198
0.9103	High Similarity	NPC183672
0.9103	High Similarity	NPC124155
0.9103	High Similarity	NPC257566
0.9097	High Similarity	NPC47923
0.9091	High Similarity	NPC472459
0.9091	High Similarity	NPC138811
0.9091	High Similarity	NPC43761
0.9091	High Similarity	NPC22062
0.9091	High Similarity	NPC41121
0.9091	High Similarity	NPC111929
0.9091	High Similarity	NPC104677
0.9091	High Similarity	NPC320283
0.9091	High Similarity	NPC308265
0.9091	High Similarity	NPC473634
0.9085	High Similarity	NPC127406
0.9085	High Similarity	NPC170475
0.9085	High Similarity	NPC261866
0.9085	High Similarity	NPC203500
0.9085	High Similarity	NPC323593
0.9085	High Similarity	NPC307938
0.9073	High Similarity	NPC318424
0.906	High Similarity	NPC201731
0.906	High Similarity	NPC97716
0.906	High Similarity	NPC237635
0.906	High Similarity	NPC104406
0.906	High Similarity	NPC24673
0.906	High Similarity	NPC79469
0.9054	High Similarity	NPC319752
0.9051	High Similarity	NPC471288
0.9038	High Similarity	NPC259834
0.9038	High Similarity	NPC27942
0.9034	High Similarity	NPC12175
0.9034	High Similarity	NPC55162
0.9034	High Similarity	NPC309154
0.9034	High Similarity	NPC90665
0.9034	High Similarity	NPC279668
0.9034	High Similarity	NPC278323
0.9032	High Similarity	NPC187379
0.9032	High Similarity	NPC473623
0.9032	High Similarity	NPC97285
0.9032	High Similarity	NPC142860
0.9032	High Similarity	NPC271479
0.9032	High Similarity	NPC472320
0.9032	High Similarity	NPC246469
0.9032	High Similarity	NPC153342
0.9032	High Similarity	NPC271270
0.9028	High Similarity	NPC234133
0.9028	High Similarity	NPC231772
0.9028	High Similarity	NPC473887
0.9028	High Similarity	NPC194281
0.9028	High Similarity	NPC127447
0.9028	High Similarity	NPC47815
0.9028	High Similarity	NPC29353
0.9028	High Similarity	NPC124784
0.9026	High Similarity	NPC197304
0.9026	High Similarity	NPC78263
0.9026	High Similarity	NPC135391
0.9026	High Similarity	NPC133671
0.9026	High Similarity	NPC77672
0.9026	High Similarity	NPC54802
0.9026	High Similarity	NPC122809
0.9026	High Similarity	NPC23817
0.9026	High Similarity	NPC43638
0.902	High Similarity	NPC470604
0.902	High Similarity	NPC470603
0.902	High Similarity	NPC470605
0.9013	High Similarity	NPC88484
0.9013	High Similarity	NPC259767
0.9007	High Similarity	NPC471984
0.9007	High Similarity	NPC191154
0.9	High Similarity	NPC6511
0.8993	High Similarity	NPC474161
0.8993	High Similarity	NPC476088
0.8986	High Similarity	NPC113770
0.8981	High Similarity	NPC243930
0.8981	High Similarity	NPC88023
0.8981	High Similarity	NPC19709
0.8981	High Similarity	NPC309025
0.8974	High Similarity	NPC163242
0.8974	High Similarity	NPC129217
0.8974	High Similarity	NPC181465
0.8974	High Similarity	NPC265885
0.8974	High Similarity	NPC85707
0.8974	High Similarity	NPC224530
0.8974	High Similarity	NPC48093
0.8974	High Similarity	NPC276377
0.8974	High Similarity	NPC473438
0.8974	High Similarity	NPC215710
0.8974	High Similarity	NPC216496
0.8974	High Similarity	NPC249281
0.8974	High Similarity	NPC476215
0.8974	High Similarity	NPC116458
0.8974	High Similarity	NPC173582
0.8974	High Similarity	NPC259957
0.8974	High Similarity	NPC159579
0.8974	High Similarity	NPC253788
0.8974	High Similarity	NPC282169
0.8974	High Similarity	NPC246943
0.8974	High Similarity	NPC101636
0.8974	High Similarity	NPC139320
0.8973	High Similarity	NPC20709
0.8973	High Similarity	NPC222342
0.8973	High Similarity	NPC265871
0.8973	High Similarity	NPC150648
0.8973	High Similarity	NPC329203
0.8973	High Similarity	NPC78913
0.8973	High Similarity	NPC274784
0.8973	High Similarity	NPC18260
0.8973	High Similarity	NPC225153
0.8973	High Similarity	NPC310135
0.8966	High Similarity	NPC181124
0.8966	High Similarity	NPC294409
0.8966	High Similarity	NPC116632
0.8966	High Similarity	NPC303644
0.8966	High Similarity	NPC266597
0.8966	High Similarity	NPC228661
0.8966	High Similarity	NPC162680
0.8966	High Similarity	NPC7013
0.8966	High Similarity	NPC209560
0.8966	High Similarity	NPC250266
0.8961	High Similarity	NPC211482
0.8961	High Similarity	NPC295613
0.8961	High Similarity	NPC473657
0.8961	High Similarity	NPC476652
0.8954	High Similarity	NPC211158
0.8954	High Similarity	NPC87304
0.8954	High Similarity	NPC268950
0.8954	High Similarity	NPC108706
0.8954	High Similarity	NPC78021
0.8947	High Similarity	NPC190217
0.8947	High Similarity	NPC325429
0.8947	High Similarity	NPC134819
0.894	High Similarity	NPC277032
0.894	High Similarity	NPC474052
0.894	High Similarity	NPC5173
0.8938	High Similarity	NPC105511
0.8933	High Similarity	NPC473077
0.8933	High Similarity	NPC296998
0.8931	High Similarity	NPC229729
0.8926	High Similarity	NPC234629
0.8926	High Similarity	NPC184649
0.8926	High Similarity	NPC311741
0.8926	High Similarity	NPC303185
0.8926	High Similarity	NPC311144
0.8924	High Similarity	NPC22832
0.8924	High Similarity	NPC311830
0.8919	High Similarity	NPC299080
0.8919	High Similarity	NPC266725
0.8919	High Similarity	NPC78803
0.8919	High Similarity	NPC217083

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 NPC471291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	932
0.2-0.3	1781
0.3-0.4	2689
0.4-0.5	1873
0.5-0.6	981
0.6-0.7	321
0.7-0.8	121
0.8-0.85	41
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9276	High Similarity	NPD4381	Clinical (unspecified phase)
0.8875	High Similarity	NPD7804	Clinical (unspecified phase)
0.8836	High Similarity	NPD1552	Clinical (unspecified phase)
0.8836	High Similarity	NPD1550	Clinical (unspecified phase)
0.8828	High Similarity	NPD1510	Phase 2
0.8812	High Similarity	NPD3818	Discontinued
0.88	High Similarity	NPD4378	Clinical (unspecified phase)
0.8776	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD7054	Approved
0.8704	High Similarity	NPD7074	Phase 3
0.8704	High Similarity	NPD7472	Approved
0.865	High Similarity	NPD6797	Phase 2
0.8645	High Similarity	NPD1934	Approved
0.8639	High Similarity	NPD2796	Approved
0.8636	High Similarity	NPD4380	Phase 2
0.8598	High Similarity	NPD7251	Discontinued
0.859	High Similarity	NPD2801	Approved
0.8553	High Similarity	NPD7410	Clinical (unspecified phase)
0.8552	High Similarity	NPD1240	Approved
0.8545	High Similarity	NPD7808	Phase 3
0.8545	High Similarity	NPD4338	Clinical (unspecified phase)
0.8544	High Similarity	NPD7075	Discontinued
0.8487	Intermediate Similarity	NPD6799	Approved
0.8487	Intermediate Similarity	NPD1511	Approved
0.8471	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7411	Suspended
0.8435	Intermediate Similarity	NPD1607	Approved
0.8418	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD3750	Approved
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.8377	Intermediate Similarity	NPD1512	Approved
0.8365	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD5403	Approved
0.8312	Intermediate Similarity	NPD5401	Approved
0.8302	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8263	Intermediate Similarity	NPD6559	Discontinued
0.8239	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8199	Intermediate Similarity	NPD3749	Approved
0.8187	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1551	Phase 2
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD3748	Approved
0.8041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD920	Approved
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7871	Intermediate Similarity	NPD1243	Approved
0.7862	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2344	Approved
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7848	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD5953	Discontinued
0.777	Intermediate Similarity	NPD2798	Approved
0.7764	Intermediate Similarity	NPD7458	Discontinued
0.7763	Intermediate Similarity	NPD1933	Approved
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7711	Intermediate Similarity	NPD919	Approved
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7703	Intermediate Similarity	NPD1203	Approved
0.7697	Intermediate Similarity	NPD943	Approved
0.7688	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7676	Intermediate Similarity	NPD7584	Approved
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4908	Phase 1
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD2309	Approved
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.7639	Intermediate Similarity	NPD1548	Phase 1
0.7635	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7613	Intermediate Similarity	NPD7033	Discontinued
0.7597	Intermediate Similarity	NPD6651	Approved
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7566	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3268	Approved
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7551	Intermediate Similarity	NPD422	Phase 1
0.7551	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6832	Phase 2
0.7546	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD8455	Phase 2
0.7467	Intermediate Similarity	NPD2797	Approved
0.7452	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6100	Approved
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6779	Approved
0.7425	Intermediate Similarity	NPD4288	Approved
0.7419	Intermediate Similarity	NPD447	Suspended
0.7419	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5124	Phase 1
0.7419	Intermediate Similarity	NPD230	Phase 1
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7384	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD1653	Approved
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD3267	Approved
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7685	Pre-registration
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7326	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7279	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7585	Approved
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4307	Phase 2
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7239	Intermediate Similarity	NPD7390	Discontinued
0.7238	Intermediate Similarity	NPD4287	Approved
0.7228	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4361	Phase 2
0.7226	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD1296	Phase 2
0.7211	Intermediate Similarity	NPD7583	Approved
0.7205	Intermediate Similarity	NPD2654	Approved
0.72	Intermediate Similarity	NPD1091	Approved
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD6823	Phase 2
0.7174	Intermediate Similarity	NPD6535	Approved
0.7174	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD7701	Phase 2
0.7168	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD5711	Approved
0.7167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9493	Approved
0.7118	Intermediate Similarity	NPD2296	Approved
0.7117	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD411	Approved
0.7101	Intermediate Similarity	NPD6844	Discontinued
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7098	Intermediate Similarity	NPD7874	Approved
0.7098	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.707	Intermediate Similarity	NPD6233	Phase 2
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7067	Intermediate Similarity	NPD17	Approved
0.7063	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7801	Approved
0.7059	Intermediate Similarity	NPD7700	Phase 2
0.7059	Intermediate Similarity	NPD7699	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data