NPASS Compound

Structure

CID161650 OpenBabel06191715532D 37 40 0 0 1 0 0 0 0 0999 V2000 -6.8563 1.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7393 -0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8934 2.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4307 3.4303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6332 -4.2052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1710 -3.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9740 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2544 1.7570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0912 0.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6833 0.9711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -1.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5241 -1.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 -2.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8423 -2.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3671 -1.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8565 0.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8595 2.6445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2044 -3.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2086 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6831 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8410 -1.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5243 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2088 -1.4570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5252 -1.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5250 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3667 0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8412 -0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6836 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8421 -1.4577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8419 -0.4856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3904 0.0135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0916 -1.9665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3665 1.0201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6835 1.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8417 0.5144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6840 -1.9433 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 29 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 25 2 0 0 0 0 24 36 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 33 1 0 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 28 34 2 0 0 0 0 29 30 1 6 0 0 0 29 36 1 0 0 0 0 30 35 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.23
Volume:	528.377
LogP:	7.766
LogD:	3.916
LogS:	-3.059
# Rotatable Bonds:	6
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	4.484
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.939
MDCK Permeability:	1.1698842172336299e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	81.64124298095703%
Volume Distribution (VD):	2.955
Pgp-substrate:	14.103606224060059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.343
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.746
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.694
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	12.316
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.283
Skin Sensitization:	0.83
Carcinogencity:	0.159
Eye Corrosion:	0.003
Eye Irritation:	0.376
Respiratory Toxicity:	0.722

Download Data

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

Natural Product: NPC161650

Natural Product ID:	NPC161650
*Common Name:**	Sorocein F
IUPAC Name:	(5aR,10aS)-1,3,8,10a-tetrahydroxy-2,5a,9-tris(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
Synonyms:	Sorocein F
Standard InCHIKey:	NVONLTGCBHODBW-LOYHVIPDSA-N
Standard InCHI:	InChI=1S/C30H34O7/c1-16(2)7-9-19-23(32)15-24-25(26(19)33)28(34)30(35)29(36-24,14-13-18(5)6)21-11-12-22(31)20(27(21)37-30)10-8-17(3)4/h7-8,11-13,15,31-33,35H,9-10,14H2,1-6H3/t29-,30-/m1/s1
SMILES:	CC(=CCc1c(cc2c(c1O)C(=O)[C@@]1([C@@](CC=C(C)C)(c3ccc(c(CC=C(C)C)c3O1)O)O2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459820
PubChem CID:	44559966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO839	Sorocea ilicifolia	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO839	Sorocea ilicifolia	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8038	Pachliopta aristolochiae	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2322	Oryctes nevadensis	Species	Solanaceae	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
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	47000.0	nM	PMID[534000]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	49000.0	nM	PMID[534000]
NPT27	Others	Unspecified		CC50	=	110000.0	nM	PMID[534000]
NPT27	Others	Unspecified		Ratio	=	2.3	n.a.	PMID[534000]

☑ 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 NPC161650 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	408
0.1-0.2	1563
0.2-0.3	3718
0.3-0.4	9292
0.4-0.5	9232
0.5-0.6	3822
0.6-0.7	5874
0.7-0.8	5370
0.8-0.85	2655
0.85-0.9	697
0.9-0.95	61
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC172687
0.9801	High Similarity	NPC311574
0.9801	High Similarity	NPC264932
0.9735	High Similarity	NPC210048
0.9408	High Similarity	NPC209760
0.9408	High Similarity	NPC100134
0.9367	High Similarity	NPC292233
0.9355	High Similarity	NPC306978
0.9342	High Similarity	NPC210597
0.9276	High Similarity	NPC472636
0.9255	High Similarity	NPC73899
0.9255	High Similarity	NPC147363
0.9255	High Similarity	NPC17105
0.9255	High Similarity	NPC474276
0.9236	High Similarity	NPC93215
0.9221	High Similarity	NPC469934
0.9221	High Similarity	NPC476169
0.9221	High Similarity	NPC471116
0.9216	High Similarity	NPC477957
0.9216	High Similarity	NPC473996
0.9216	High Similarity	NPC138288
0.9161	High Similarity	NPC215917
0.9161	High Similarity	NPC20530
0.9161	High Similarity	NPC10754
0.9156	High Similarity	NPC311579
0.9156	High Similarity	NPC293286
0.9156	High Similarity	NPC236756
0.915	High Similarity	NPC471677
0.915	High Similarity	NPC262039
0.915	High Similarity	NPC472580
0.915	High Similarity	NPC471229
0.915	High Similarity	NPC319910
0.915	High Similarity	NPC254412
0.915	High Similarity	NPC278476
0.915	High Similarity	NPC262038
0.915	High Similarity	NPC471675
0.9145	High Similarity	NPC277032
0.9139	High Similarity	NPC472918
0.9133	High Similarity	NPC71210
0.9097	High Similarity	NPC48579
0.9097	High Similarity	NPC207809
0.9097	High Similarity	NPC259710
0.9097	High Similarity	NPC304207
0.9097	High Similarity	NPC217706
0.9091	High Similarity	NPC217149
0.9091	High Similarity	NPC476238
0.9091	High Similarity	NPC243171
0.9091	High Similarity	NPC216035
0.9091	High Similarity	NPC31627
0.9091	High Similarity	NPC35567
0.9091	High Similarity	NPC171651
0.9091	High Similarity	NPC327269
0.9085	High Similarity	NPC105136
0.9085	High Similarity	NPC472421
0.9085	High Similarity	NPC267117
0.9079	High Similarity	NPC296869
0.9073	High Similarity	NPC178343
0.9073	High Similarity	NPC5820
0.9073	High Similarity	NPC306488
0.9073	High Similarity	NPC124729
0.9067	High Similarity	NPC190637
0.9067	High Similarity	NPC212932
0.9067	High Similarity	NPC9117
0.9067	High Similarity	NPC293053
0.9067	High Similarity	NPC24821
0.906	High Similarity	NPC310128
0.9057	High Similarity	NPC179198
0.9057	High Similarity	NPC183672
0.9057	High Similarity	NPC278419
0.9057	High Similarity	NPC66087
0.9038	High Similarity	NPC146636
0.9032	High Similarity	NPC180301
0.9032	High Similarity	NPC248793
0.9026	High Similarity	NPC472423
0.9026	High Similarity	NPC244577
0.9026	High Similarity	NPC263384
0.9026	High Similarity	NPC471676
0.9026	High Similarity	NPC474772
0.9026	High Similarity	NPC472420
0.9026	High Similarity	NPC474744
0.9026	High Similarity	NPC472422
0.902	High Similarity	NPC472628
0.9013	High Similarity	NPC14001
0.9013	High Similarity	NPC166757
0.9012	High Similarity	NPC8704
0.9012	High Similarity	NPC287884
0.9007	High Similarity	NPC326500
0.9007	High Similarity	NPC216538
0.9007	High Similarity	NPC273538
0.9	High Similarity	NPC266725
0.9	High Similarity	NPC144499
0.9	High Similarity	NPC200694
0.9	High Similarity	NPC473042
0.9	High Similarity	NPC471520
0.8994	High Similarity	NPC131745
0.8994	High Similarity	NPC259834
0.8994	High Similarity	NPC150164
0.8974	High Similarity	NPC108937
0.8974	High Similarity	NPC279218
0.8974	High Similarity	NPC477958
0.8974	High Similarity	NPC111341
0.8974	High Similarity	NPC304745
0.8968	High Similarity	NPC475790
0.8968	High Similarity	NPC285623
0.8968	High Similarity	NPC142527
0.8954	High Similarity	NPC244407
0.8954	High Similarity	NPC145467
0.8951	High Similarity	NPC5319
0.8947	High Similarity	NPC220418
0.8947	High Similarity	NPC229190
0.8947	High Similarity	NPC477955
0.894	High Similarity	NPC18585
0.894	High Similarity	NPC219915
0.894	High Similarity	NPC166138
0.894	High Similarity	NPC106985
0.894	High Similarity	NPC158874
0.8938	High Similarity	NPC471286
0.8938	High Similarity	NPC472581
0.8931	High Similarity	NPC92589
0.8924	High Similarity	NPC470607
0.8917	High Similarity	NPC129053
0.8917	High Similarity	NPC109967
0.8917	High Similarity	NPC476652
0.8917	High Similarity	NPC475797
0.8917	High Similarity	NPC78554
0.8917	High Similarity	NPC321372
0.8917	High Similarity	NPC469936
0.8917	High Similarity	NPC211482
0.8917	High Similarity	NPC474609
0.8917	High Similarity	NPC474738
0.891	High Similarity	NPC268193
0.891	High Similarity	NPC20907
0.891	High Similarity	NPC244250
0.891	High Similarity	NPC189130
0.891	High Similarity	NPC472583
0.891	High Similarity	NPC7989
0.891	High Similarity	NPC223701
0.891	High Similarity	NPC203080
0.8903	High Similarity	NPC474021
0.8903	High Similarity	NPC474023
0.8903	High Similarity	NPC295650
0.8903	High Similarity	NPC318424
0.8896	High Similarity	NPC269420
0.8896	High Similarity	NPC477941
0.8896	High Similarity	NPC470461
0.8889	High Similarity	NPC476459
0.8889	High Similarity	NPC472627
0.8889	High Similarity	NPC44721
0.8889	High Similarity	NPC476182
0.8889	High Similarity	NPC91902
0.8889	High Similarity	NPC14875
0.8889	High Similarity	NPC176869
0.8889	High Similarity	NPC122828
0.8889	High Similarity	NPC211466
0.8889	High Similarity	NPC3779
0.8889	High Similarity	NPC308200
0.8889	High Similarity	NPC40086
0.8882	High Similarity	NPC259007
0.8882	High Similarity	NPC72016
0.8882	High Similarity	NPC204088
0.8882	High Similarity	NPC329215
0.8882	High Similarity	NPC271288
0.8875	High Similarity	NPC219861
0.8875	High Similarity	NPC475106
0.8869	High Similarity	NPC106700
0.8868	High Similarity	NPC470183
0.8868	High Similarity	NPC153342
0.8868	High Similarity	NPC472624
0.8867	High Similarity	NPC69769
0.8867	High Similarity	NPC477272
0.8861	High Similarity	NPC273843
0.8861	High Similarity	NPC237418
0.8861	High Similarity	NPC6985
0.8861	High Similarity	NPC23817
0.8861	High Similarity	NPC288084
0.8861	High Similarity	NPC470606
0.8854	High Similarity	NPC275575
0.8854	High Similarity	NPC133392
0.8846	High Similarity	NPC63187
0.8846	High Similarity	NPC161881
0.8846	High Similarity	NPC150123
0.8846	High Similarity	NPC37684
0.8846	High Similarity	NPC45934
0.8846	High Similarity	NPC56232
0.8846	High Similarity	NPC10807
0.8846	High Similarity	NPC244583
0.8846	High Similarity	NPC157784
0.8841	High Similarity	NPC477529
0.8839	High Similarity	NPC29777
0.8839	High Similarity	NPC321896
0.8839	High Similarity	NPC471984
0.8839	High Similarity	NPC476185
0.8839	High Similarity	NPC61258
0.8839	High Similarity	NPC471115
0.8839	High Similarity	NPC476509
0.8831	High Similarity	NPC168085
0.8831	High Similarity	NPC39195
0.8831	High Similarity	NPC470460
0.8827	High Similarity	NPC323137
0.8827	High Similarity	NPC82330

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 NPC161650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	910
0.2-0.3	1636
0.3-0.4	2689
0.4-0.5	1940
0.5-0.6	1049
0.6-0.7	384
0.7-0.8	153
0.8-0.85	31
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD7075	Discontinued
0.9032	High Similarity	NPD7096	Clinical (unspecified phase)
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.8951	High Similarity	NPD7804	Clinical (unspecified phase)
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.8599	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD3882	Suspended
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.85	High Similarity	NPD8443	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD1934	Approved
0.8481	Intermediate Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD1512	Approved
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8393	Intermediate Similarity	NPD6797	Phase 2
0.8385	Intermediate Similarity	NPD3817	Phase 2
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8313	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6166	Phase 2
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD2800	Approved
0.8282	Intermediate Similarity	NPD3749	Approved
0.8274	Intermediate Similarity	NPD7054	Approved
0.8225	Intermediate Similarity	NPD7472	Approved
0.8187	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5494	Approved
0.817	Intermediate Similarity	NPD1510	Phase 2
0.8146	Intermediate Similarity	NPD1240	Approved
0.8117	Intermediate Similarity	NPD2796	Approved
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5403	Approved
0.8047	Intermediate Similarity	NPD7473	Discontinued
0.8039	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8024	Intermediate Similarity	NPD6959	Discontinued
0.8023	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6232	Discontinued
0.7962	Intermediate Similarity	NPD1243	Approved
0.7939	Intermediate Similarity	NPD5402	Approved
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7937	Intermediate Similarity	NPD5401	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.7892	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD920	Approved
0.7834	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7811	Intermediate Similarity	NPD1247	Approved
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6100	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6099	Approved
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3748	Approved
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD2309	Approved
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3226	Approved
0.7632	Intermediate Similarity	NPD2798	Approved
0.7628	Intermediate Similarity	NPD6355	Discontinued
0.7622	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7598	Intermediate Similarity	NPD8434	Phase 2
0.7594	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2403	Approved
0.7566	Intermediate Similarity	NPD7584	Approved
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7458	Discontinued
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7527	Intermediate Similarity	NPD6782	Approved
0.7527	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD6776	Approved
0.7527	Intermediate Similarity	NPD6777	Approved
0.7527	Intermediate Similarity	NPD6779	Approved
0.7527	Intermediate Similarity	NPD6781	Approved
0.7527	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7456	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD5049	Phase 3
0.7452	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.7439	Intermediate Similarity	NPD7390	Discontinued
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7436	Intermediate Similarity	NPD3268	Approved
0.7423	Intermediate Similarity	NPD2354	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7419	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7696	Phase 3
0.7407	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD7698	Approved
0.7405	Intermediate Similarity	NPD1933	Approved
0.7391	Intermediate Similarity	NPD1471	Phase 3
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7372	Intermediate Similarity	NPD7095	Approved
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD7871	Phase 2
0.7358	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7874	Approved
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7355	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7344	Intermediate Similarity	NPD7701	Phase 2
0.7342	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD2797	Approved
0.7337	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3764	Approved
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4287	Approved
0.7312	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4361	Phase 2
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7294	Intermediate Similarity	NPD37	Approved
0.7288	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7258	Intermediate Similarity	NPD6535	Approved
0.7258	Intermediate Similarity	NPD6534	Approved
0.7255	Intermediate Similarity	NPD9717	Approved
0.7249	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7234	Intermediate Similarity	NPD7700	Phase 2
0.7234	Intermediate Similarity	NPD7699	Phase 2
0.7233	Intermediate Similarity	NPD1613	Approved
0.7233	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7801	Approved
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7195	Intermediate Similarity	NPD2654	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8319	Approved
0.7188	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5124	Phase 1
0.7188	Intermediate Similarity	NPD8320	Phase 1
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2353	Approved
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7165	Intermediate Similarity	NPD7585	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7113	Intermediate Similarity	NPD7583	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.711	Intermediate Similarity	NPD4288	Approved
0.711	Intermediate Similarity	NPD2296	Approved
0.7108	Intermediate Similarity	NPD3887	Approved
0.7108	Intermediate Similarity	NPD6190	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