NPASS Compound

Structure

NPC30655 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 1.0000 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 -2.5981 1.5000 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 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6369 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6369 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 -0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 10 2 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 4 13 1 0 0 0 0 5 12 1 0 0 0 0 5 14 2 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	328.45
LogP:	4.296
LogD:	2.954
LogS:	-3.839
# Rotatable Bonds:	1
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	3.306
Fsp3:	0.263
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:	-5.024
MDCK Permeability:	1.1769935554184485e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	97.88416290283203%
Volume Distribution (VD):	0.762
Pgp-substrate:	2.225809097290039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.523
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.629
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	8.499
Half-life (T1/2):	0.454

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.487
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.871
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.106
Respiratory Toxicity:	0.842

Download Data

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

Natural Product: NPC30655

Natural Product ID:	NPC30655
*Common Name:**	Moracin P
IUPAC Name:	5-[(6R)-6-hydroxy-7,7-dimethyl-5,6-dihydrofuro[3,2-g]chromen-2-yl]benzene-1,3-diol
Synonyms:	(-)-Moracin P; Moracin P
Standard InCHIKey:	QFUCSEIKNTUPPA-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C19H18O5/c1-19(2)18(22)7-11-3-10-6-15(23-16(10)9-17(11)24-19)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3/t18-/m1/s1
SMILES:	CC1(C)[C@@H](Cc2cc3cc(c4cc(cc(c4)O)O)oc3cc2O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561971
PubChem CID:	25208124
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO30392	Morus	Genus	Sulidae	Eukaryota	root bark	n.a.	n.a.	PMID[16356713]
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072214]
NPO30392	Morus	Genus	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21319773]
NPO30392	Morus	Genus	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22297755]
NPO2578	Morus sp.	Species	Sulidae	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	7

Activity Type	# Activity
CELL-LINE	1
Individual Protein	4
Others	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	80000.0	nM	PMID[564685]
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	IC50	>	80000.0	nM	PMID[564685]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	0.65	nM	PMID[564686]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	10.7	nM	PMID[564687]
NPT2	Others	Unspecified		IC50	>	80000.0	nM	PMID[564685]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	10600.0	nM	PMID[564686]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[564686]

☑ 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 NPC30655 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	391
0.1-0.2	1607
0.2-0.3	3601
0.3-0.4	8870
0.4-0.5	9666
0.5-0.6	3789
0.6-0.7	5016
0.7-0.8	4956
0.8-0.85	2535
0.85-0.9	2015
0.9-0.95	246
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC45124
1.0	High Similarity	NPC74854
0.9675	High Similarity	NPC220582
0.9675	High Similarity	NPC304839
0.949	High Similarity	NPC472581
0.9434	High Similarity	NPC476459
0.9412	High Similarity	NPC473996
0.9412	High Similarity	NPC5871
0.9371	High Similarity	NPC53640
0.9367	High Similarity	NPC124038
0.9355	High Similarity	NPC208152
0.9355	High Similarity	NPC78492
0.9351	High Similarity	NPC183874
0.9351	High Similarity	NPC1477
0.9351	High Similarity	NPC469405
0.9351	High Similarity	NPC472462
0.9351	High Similarity	NPC213608
0.9346	High Similarity	NPC472422
0.9346	High Similarity	NPC472420
0.9346	High Similarity	NPC471676
0.9346	High Similarity	NPC472423
0.9346	High Similarity	NPC263384
0.9346	High Similarity	NPC472580
0.9346	High Similarity	NPC472636
0.9346	High Similarity	NPC474744
0.9346	High Similarity	NPC244577
0.9346	High Similarity	NPC474772
0.9346	High Similarity	NPC170169
0.9342	High Similarity	NPC178202
0.9308	High Similarity	NPC37183
0.9304	High Similarity	NPC219861
0.9299	High Similarity	NPC471976
0.9295	High Similarity	NPC65504
0.929	High Similarity	NPC198490
0.9286	High Similarity	NPC31627
0.9286	High Similarity	NPC476238
0.9286	High Similarity	NPC285623
0.9286	High Similarity	NPC477957
0.9286	High Similarity	NPC327269
0.9281	High Similarity	NPC230713
0.9281	High Similarity	NPC78335
0.9281	High Similarity	NPC472421
0.9259	High Similarity	NPC472584
0.925	High Similarity	NPC119589
0.925	High Similarity	NPC277480
0.9241	High Similarity	NPC3629
0.9236	High Similarity	NPC40583
0.9226	High Similarity	NPC122365
0.9226	High Similarity	NPC7989
0.9226	High Similarity	NPC472583
0.9226	High Similarity	NPC223701
0.9221	High Similarity	NPC474021
0.9221	High Similarity	NPC471677
0.9221	High Similarity	NPC474023
0.9221	High Similarity	NPC471675
0.9216	High Similarity	NPC296030
0.9216	High Similarity	NPC37226
0.9216	High Similarity	NPC226644
0.9216	High Similarity	NPC39929
0.9211	High Similarity	NPC17816
0.9202	High Similarity	NPC310794
0.9198	High Similarity	NPC120220
0.9198	High Similarity	NPC131866
0.9193	High Similarity	NPC247973
0.9187	High Similarity	NPC300053
0.9187	High Similarity	NPC108433
0.9182	High Similarity	NPC472635
0.9177	High Similarity	NPC328102
0.9177	High Similarity	NPC472624
0.9177	High Similarity	NPC470810
0.9172	High Similarity	NPC196448
0.9172	High Similarity	NPC268360
0.9167	High Similarity	NPC477958
0.9167	High Similarity	NPC148938
0.9161	High Similarity	NPC171651
0.9161	High Similarity	NPC243171
0.9161	High Similarity	NPC35567
0.9161	High Similarity	NPC475790
0.9145	High Similarity	NPC290133
0.9145	High Similarity	NPC187282
0.9145	High Similarity	NPC24136
0.9136	High Similarity	NPC53252
0.9125	High Similarity	NPC18100
0.9119	High Similarity	NPC134783
0.9114	High Similarity	NPC476349
0.9114	High Similarity	NPC476350
0.9114	High Similarity	NPC473990
0.9108	High Similarity	NPC180924
0.9103	High Similarity	NPC293286
0.9103	High Similarity	NPC74924
0.9103	High Similarity	NPC72370
0.9103	High Similarity	NPC235333
0.9097	High Similarity	NPC106372
0.9097	High Similarity	NPC262039
0.9097	High Similarity	NPC262038
0.9097	High Similarity	NPC58668
0.9097	High Similarity	NPC254412
0.9097	High Similarity	NPC278476
0.9097	High Similarity	NPC319910
0.9091	High Similarity	NPC37208
0.9091	High Similarity	NPC221868
0.9091	High Similarity	NPC89442
0.9091	High Similarity	NPC317492
0.9091	High Similarity	NPC472628
0.9085	High Similarity	NPC12148
0.9085	High Similarity	NPC470670
0.9085	High Similarity	NPC202494
0.9085	High Similarity	NPC47388
0.9085	High Similarity	NPC85773
0.9085	High Similarity	NPC473133
0.9085	High Similarity	NPC130581
0.9085	High Similarity	NPC91902
0.9085	High Similarity	NPC14875
0.9085	High Similarity	NPC472627
0.9079	High Similarity	NPC470890
0.9068	High Similarity	NPC472277
0.9062	High Similarity	NPC474033
0.9062	High Similarity	NPC474034
0.9062	High Similarity	NPC81679
0.9062	High Similarity	NPC476247
0.9062	High Similarity	NPC472402
0.9057	High Similarity	NPC472631
0.9057	High Similarity	NPC174953
0.9057	High Similarity	NPC475784
0.9057	High Similarity	NPC472630
0.9051	High Similarity	NPC27337
0.9051	High Similarity	NPC212967
0.9051	High Similarity	NPC260902
0.9051	High Similarity	NPC474055
0.9051	High Similarity	NPC246647
0.9051	High Similarity	NPC96342
0.9051	High Similarity	NPC296957
0.9051	High Similarity	NPC164110
0.9051	High Similarity	NPC472598
0.9051	High Similarity	NPC291508
0.9045	High Similarity	NPC321779
0.9045	High Similarity	NPC259710
0.9045	High Similarity	NPC207809
0.9045	High Similarity	NPC217706
0.9045	High Similarity	NPC304207
0.9045	High Similarity	NPC45849
0.9045	High Similarity	NPC200761
0.9045	High Similarity	NPC477530
0.9045	High Similarity	NPC470681
0.9045	High Similarity	NPC297531
0.9045	High Similarity	NPC470327
0.9045	High Similarity	NPC477503
0.9045	High Similarity	NPC48579
0.9045	High Similarity	NPC213936
0.9045	High Similarity	NPC99199
0.9038	High Similarity	NPC256141
0.9038	High Similarity	NPC56232
0.9038	High Similarity	NPC150123
0.9038	High Similarity	NPC207624
0.9038	High Similarity	NPC106976
0.9038	High Similarity	NPC216035
0.9038	High Similarity	NPC217149
0.9038	High Similarity	NPC253872
0.9038	High Similarity	NPC244583
0.9038	High Similarity	NPC161881
0.9038	High Similarity	NPC210597
0.9038	High Similarity	NPC10807
0.9038	High Similarity	NPC138288
0.9032	High Similarity	NPC167576
0.9032	High Similarity	NPC472633
0.9032	High Similarity	NPC105136
0.9026	High Similarity	NPC272194
0.9026	High Similarity	NPC10097
0.9026	High Similarity	NPC168085
0.9026	High Similarity	NPC135325
0.902	High Similarity	NPC474302
0.902	High Similarity	NPC300267
0.902	High Similarity	NPC316769
0.902	High Similarity	NPC210826
0.902	High Similarity	NPC472629
0.902	High Similarity	NPC51641
0.9018	High Similarity	NPC288813
0.9012	High Similarity	NPC235610
0.9012	High Similarity	NPC170245
0.9006	High Similarity	NPC472281
0.9006	High Similarity	NPC472278
0.9006	High Similarity	NPC473313
0.9006	High Similarity	NPC329669
0.9006	High Similarity	NPC205265
0.9	High Similarity	NPC472634
0.9	High Similarity	NPC472632
0.9	High Similarity	NPC14822
0.9	High Similarity	NPC474038
0.9	High Similarity	NPC142252
0.9	High Similarity	NPC92589
0.8994	High Similarity	NPC22192
0.8994	High Similarity	NPC196879
0.8987	High Similarity	NPC164427
0.8987	High Similarity	NPC10754
0.8987	High Similarity	NPC195796
0.8987	High Similarity	NPC45131
0.8987	High Similarity	NPC209614
0.8987	High Similarity	NPC20530
0.8987	High Similarity	NPC470328
0.8987	High Similarity	NPC35038

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 NPC30655 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	908
0.2-0.3	1740
0.3-0.4	2584
0.4-0.5	1900
0.5-0.6	1064
0.6-0.7	396
0.7-0.8	146
0.8-0.85	39
0.85-0.9	24
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD2393	Clinical (unspecified phase)
0.897	High Similarity	NPD6559	Discontinued
0.891	High Similarity	NPD4380	Phase 2
0.8797	High Similarity	NPD1934	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.8634	High Similarity	NPD3882	Suspended
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8614	High Similarity	NPD3818	Discontinued
0.8606	High Similarity	NPD6168	Clinical (unspecified phase)
0.8606	High Similarity	NPD6167	Clinical (unspecified phase)
0.8606	High Similarity	NPD6166	Phase 2
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8589	High Similarity	NPD5494	Approved
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD6959	Discontinued
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8509	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3749	Approved
0.8457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6801	Discontinued
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8343	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD2796	Approved
0.8294	Intermediate Similarity	NPD7074	Phase 3
0.8291	Intermediate Similarity	NPD1511	Approved
0.825	Intermediate Similarity	NPD920	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8235	Intermediate Similarity	NPD7054	Approved
0.8204	Intermediate Similarity	NPD1247	Approved
0.8187	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD7472	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6232	Discontinued
0.8153	Intermediate Similarity	NPD1243	Approved
0.8153	Intermediate Similarity	NPD2800	Approved
0.8141	Intermediate Similarity	NPD2344	Approved
0.814	Intermediate Similarity	NPD6797	Phase 2
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD2532	Approved
0.8125	Intermediate Similarity	NPD2534	Approved
0.8125	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3817	Phase 2
0.8121	Intermediate Similarity	NPD5402	Approved
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8105	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD7251	Discontinued
0.8084	Intermediate Similarity	NPD919	Approved
0.8072	Intermediate Similarity	NPD7768	Phase 2
0.8046	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7937	Intermediate Similarity	NPD2309	Approved
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5403	Approved
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7844	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD5401	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8434	Phase 2
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7673	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD1613	Approved
0.7643	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD943	Approved
0.763	Intermediate Similarity	NPD5711	Approved
0.763	Intermediate Similarity	NPD5710	Approved
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7605	Intermediate Similarity	NPD3226	Approved
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7547	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2424	Discontinued
0.7529	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD7229	Phase 3
0.7529	Intermediate Similarity	NPD5761	Phase 2
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6782	Approved
0.7486	Intermediate Similarity	NPD4287	Approved
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD37	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7458	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7448	Intermediate Similarity	NPD7584	Approved
0.7442	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7442	Intermediate Similarity	NPD4966	Approved
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4363	Phase 3
0.7419	Intermediate Similarity	NPD4360	Phase 2
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7389	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2296	Approved
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.736	Intermediate Similarity	NPD7228	Approved
0.7346	Intermediate Similarity	NPD3748	Approved
0.7345	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7342	Intermediate Similarity	NPD3027	Phase 3
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7698	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7289	Intermediate Similarity	NPD6190	Approved
0.7288	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4361	Phase 2
0.7287	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6280	Approved
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD6279	Approved
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7256	Intermediate Similarity	NPD1471	Phase 3
0.7247	Intermediate Similarity	NPD2403	Approved
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD3823	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7232	Intermediate Similarity	NPD6808	Phase 2
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7198	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD3764	Approved
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD2654	Approved
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD1653	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7104	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7072	Intermediate Similarity	NPD2163	Approved
0.707	Intermediate Similarity	NPD4749	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