NPASS Compound

Structure

NPC271945 OpenBabel07101719252D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.6831 4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7469 0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3457 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1646 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1701 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7524 0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 30 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 21 2 0 0 0 0 12 22 1 0 0 0 0 13 31 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 26 2 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 13 1 6 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 0 0 0 0 25 32 1 0 0 0 0 26 30 1 0 0 0 0 27 23 1 6 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.22
Volume:	464.182
LogP:	7.607
LogD:	4.263
LogS:	-2.856
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.148
Fsp3:	0.407
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.92
MDCK Permeability:	1.5295834600692615e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.402
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	88.04783630371094%
Volume Distribution (VD):	3.627
Pgp-substrate:	14.936992645263672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.911
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.751
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	10.804
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.933
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.707
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC271945

Natural Product ID:	NPC271945
*Common Name:**	Bicolosin A
IUPAC Name:	(6aR,11aR)-1-methoxy-8-methyl-2,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:	Bicolosin A
Standard InCHIKey:	KDEQNCVCQDEWGJ-CCLHPLFOSA-N
Standard InCHI:	InChI=1S/C27H32O5/c1-14(2)7-9-17-21(28)12-22-23(26(17)30-6)27-20(13-31-22)19-11-16(5)24(29)18(25(19)32-27)10-8-15(3)4/h7-8,11-12,20,27-29H,9-10,13H2,1-6H3/t20-,27+/m0/s1
SMILES:	COc1c(CC=C(C)C)c(O)cc2c1[C@@H]1Oc3c([C@@H]1CO2)cc(c(c3CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835715
PubChem CID:	56668791
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[21911291]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31675225]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10149	Lespedeza bicolor	Species	Fabaceae	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	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	160.0	nM	PMID[490588]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	320.0	nM	PMID[490588]

☑ 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 NPC271945 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	372
0.1-0.2	1443
0.2-0.3	3777
0.3-0.4	11461
0.4-0.5	7452
0.5-0.6	4129
0.6-0.7	7743
0.7-0.8	5100
0.8-0.85	897
0.85-0.9	200
0.9-0.95	66
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181497
0.9919	High Similarity	NPC470225
0.9919	High Similarity	NPC27187
0.984	High Similarity	NPC206224
0.984	High Similarity	NPC17343
0.984	High Similarity	NPC280653
0.984	High Similarity	NPC129106
0.984	High Similarity	NPC476166
0.984	High Similarity	NPC300875
0.984	High Similarity	NPC207892
0.984	High Similarity	NPC164574
0.984	High Similarity	NPC118114
0.984	High Similarity	NPC228369
0.984	High Similarity	NPC129784
0.984	High Similarity	NPC268917
0.984	High Similarity	NPC196765
0.984	High Similarity	NPC150011
0.984	High Similarity	NPC236014
0.984	High Similarity	NPC12875
0.9762	High Similarity	NPC13005
0.968	High Similarity	NPC93962
0.9609	High Similarity	NPC223008
0.9609	High Similarity	NPC225696
0.9609	High Similarity	NPC97834
0.9609	High Similarity	NPC198154
0.9609	High Similarity	NPC115335
0.9609	High Similarity	NPC296915
0.96	High Similarity	NPC47283
0.96	High Similarity	NPC39064
0.96	High Similarity	NPC53986
0.96	High Similarity	NPC38664
0.9531	High Similarity	NPC85435
0.9457	High Similarity	NPC124085
0.9457	High Similarity	NPC117048
0.9444	High Similarity	NPC274717
0.944	High Similarity	NPC26879
0.944	High Similarity	NPC471215
0.944	High Similarity	NPC283049
0.944	High Similarity	NPC50315
0.944	High Similarity	NPC230479
0.944	High Similarity	NPC262573
0.9389	High Similarity	NPC474687
0.9375	High Similarity	NPC118683
0.9375	High Similarity	NPC162801
0.9375	High Similarity	NPC164804
0.9375	High Similarity	NPC293203
0.9375	High Similarity	NPC68205
0.9375	High Similarity	NPC244888
0.9375	High Similarity	NPC211413
0.936	High Similarity	NPC17809
0.936	High Similarity	NPC188022
0.936	High Similarity	NPC102540
0.936	High Similarity	NPC103420
0.936	High Similarity	NPC285040
0.9318	High Similarity	NPC475836
0.9313	High Similarity	NPC262585
0.9313	High Similarity	NPC20829
0.9313	High Similarity	NPC3049
0.9313	High Similarity	NPC18189
0.9286	High Similarity	NPC276212
0.928	High Similarity	NPC86502
0.928	High Similarity	NPC106914
0.928	High Similarity	NPC256015
0.928	High Similarity	NPC197351
0.928	High Similarity	NPC134195
0.928	High Similarity	NPC294156
0.928	High Similarity	NPC246648
0.9231	High Similarity	NPC77196
0.9225	High Similarity	NPC103799
0.9206	High Similarity	NPC81641
0.92	High Similarity	NPC76465
0.92	High Similarity	NPC38761
0.9179	High Similarity	NPC5155
0.9167	High Similarity	NPC471522
0.916	High Similarity	NPC473107
0.912	High Similarity	NPC150026
0.912	High Similarity	NPC100099
0.912	High Similarity	NPC36016
0.9118	High Similarity	NPC63879
0.9098	High Similarity	NPC470308
0.9098	High Similarity	NPC470307
0.9091	High Similarity	NPC125579
0.9084	High Similarity	NPC92805
0.907	High Similarity	NPC134360
0.9062	High Similarity	NPC149796
0.9044	High Similarity	NPC102044
0.9044	High Similarity	NPC47633
0.9044	High Similarity	NPC85264
0.904	High Similarity	NPC193364
0.904	High Similarity	NPC54972
0.8992	High Similarity	NPC87224
0.8992	High Similarity	NPC222572
0.8978	High Similarity	NPC12641
0.8978	High Similarity	NPC280092
0.8978	High Similarity	NPC93323
0.8978	High Similarity	NPC45257
0.8963	High Similarity	NPC184797
0.8963	High Similarity	NPC309124
0.8963	High Similarity	NPC27495
0.8955	High Similarity	NPC477938
0.8947	High Similarity	NPC473413
0.8939	High Similarity	NPC215037
0.8913	High Similarity	NPC469557
0.8897	High Similarity	NPC263261
0.8897	High Similarity	NPC87725
0.8897	High Similarity	NPC247291
0.8889	High Similarity	NPC232164
0.8889	High Similarity	NPC236306
0.8889	High Similarity	NPC473739
0.8889	High Similarity	NPC70682
0.8889	High Similarity	NPC260741
0.8889	High Similarity	NPC32630
0.8881	High Similarity	NPC141717
0.8881	High Similarity	NPC470802
0.8881	High Similarity	NPC472800
0.888	High Similarity	NPC8283
0.888	High Similarity	NPC258979
0.888	High Similarity	NPC93398
0.8872	High Similarity	NPC476617
0.8872	High Similarity	NPC476615
0.8872	High Similarity	NPC476616
0.8864	High Similarity	NPC472798
0.8849	High Similarity	NPC260397
0.8832	High Similarity	NPC107161
0.8824	High Similarity	NPC259519
0.8806	High Similarity	NPC15109
0.8806	High Similarity	NPC11727
0.88	High Similarity	NPC59561
0.88	High Similarity	NPC172253
0.8797	High Similarity	NPC177712
0.8797	High Similarity	NPC11060
0.8797	High Similarity	NPC24913
0.8788	High Similarity	NPC472590
0.8788	High Similarity	NPC160623
0.8786	High Similarity	NPC101376
0.8786	High Similarity	NPC21776
0.8786	High Similarity	NPC16269
0.8779	High Similarity	NPC472796
0.8779	High Similarity	NPC472795
0.8779	High Similarity	NPC472797
0.8777	High Similarity	NPC181615
0.8769	High Similarity	NPC473134
0.876	High Similarity	NPC167571
0.876	High Similarity	NPC207179
0.876	High Similarity	NPC278552
0.8759	High Similarity	NPC100482
0.8759	High Similarity	NPC265075
0.8759	High Similarity	NPC35216
0.8759	High Similarity	NPC277331
0.875	High Similarity	NPC471388
0.8741	High Similarity	NPC162659
0.8741	High Similarity	NPC126101
0.8741	High Similarity	NPC234952
0.8741	High Similarity	NPC270456
0.8741	High Similarity	NPC248727
0.8741	High Similarity	NPC78047
0.8741	High Similarity	NPC173660
0.8741	High Similarity	NPC265433
0.8741	High Similarity	NPC327735
0.874	High Similarity	NPC476633
0.8732	High Similarity	NPC472710
0.8732	High Similarity	NPC472709
0.8723	High Similarity	NPC71726
0.872	High Similarity	NPC131118
0.8714	High Similarity	NPC14468
0.8705	High Similarity	NPC475492
0.8705	High Similarity	NPC50250
0.8705	High Similarity	NPC473845
0.8705	High Similarity	NPC473108
0.8702	High Similarity	NPC211179
0.8702	High Similarity	NPC38604
0.8696	High Similarity	NPC2613
0.8696	High Similarity	NPC204347
0.8696	High Similarity	NPC59841
0.8696	High Similarity	NPC475891
0.8686	High Similarity	NPC254759
0.8686	High Similarity	NPC213607
0.8686	High Similarity	NPC174787
0.8686	High Similarity	NPC182509
0.8686	High Similarity	NPC160283
0.8682	High Similarity	NPC159132
0.8672	High Similarity	NPC57199
0.8667	High Similarity	NPC234333
0.8667	High Similarity	NPC47398
0.8667	High Similarity	NPC121812
0.8667	High Similarity	NPC112939
0.8667	High Similarity	NPC260898
0.8667	High Similarity	NPC61946
0.8667	High Similarity	NPC470356
0.8667	High Similarity	NPC94750
0.8667	High Similarity	NPC195022
0.8667	High Similarity	NPC474206
0.8667	High Similarity	NPC112246
0.8667	High Similarity	NPC151224
0.8657	High Similarity	NPC469610
0.8657	High Similarity	NPC26394
0.8651	High Similarity	NPC295259
0.8647	High Similarity	NPC8899
0.8643	High Similarity	NPC180953
0.8643	High Similarity	NPC106126

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 NPC271945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	890
0.2-0.3	1641
0.3-0.4	2702
0.4-0.5	1777
0.5-0.6	1059
0.6-0.7	629
0.7-0.8	138
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9297	High Similarity	NPD4907	Clinical (unspecified phase)
0.9141	High Similarity	NPD4908	Phase 1
0.904	High Similarity	NPD1610	Phase 2
0.8626	High Similarity	NPD2861	Phase 2
0.8571	High Similarity	NPD6410	Clinical (unspecified phase)
0.8571	High Similarity	NPD1548	Phase 1
0.8496	Intermediate Similarity	NPD4625	Phase 3
0.8462	Intermediate Similarity	NPD4749	Approved
0.8444	Intermediate Similarity	NPD1613	Approved
0.8444	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD5124	Phase 1
0.8088	Intermediate Similarity	NPD3027	Phase 3
0.8067	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD7447	Phase 1
0.7917	Intermediate Similarity	NPD7466	Approved
0.7887	Intermediate Similarity	NPD6099	Approved
0.7887	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7212	Phase 2
0.7877	Intermediate Similarity	NPD7213	Phase 3
0.7852	Intermediate Similarity	NPD8651	Approved
0.7852	Intermediate Similarity	NPD6696	Suspended
0.7832	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD5588	Approved
0.7793	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD4060	Phase 1
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6671	Approved
0.7761	Intermediate Similarity	NPD422	Phase 1
0.7746	Intermediate Similarity	NPD4538	Approved
0.7746	Intermediate Similarity	NPD4536	Approved
0.7746	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7075	Discontinued
0.7687	Intermediate Similarity	NPD5058	Phase 3
0.7682	Intermediate Similarity	NPD4380	Phase 2
0.7662	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD7229	Phase 3
0.763	Intermediate Similarity	NPD1091	Approved
0.7606	Intermediate Similarity	NPD6355	Discontinued
0.7603	Intermediate Similarity	NPD6674	Discontinued
0.7586	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6005	Phase 3
0.7586	Intermediate Similarity	NPD6002	Phase 3
0.7586	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6004	Phase 3
0.7582	Intermediate Similarity	NPD37	Approved
0.7582	Intermediate Similarity	NPD1934	Approved
0.758	Intermediate Similarity	NPD6959	Discontinued
0.7569	Intermediate Similarity	NPD5960	Phase 3
0.7564	Intermediate Similarity	NPD6234	Discontinued
0.7551	Intermediate Similarity	NPD3892	Phase 2
0.7551	Intermediate Similarity	NPD3750	Approved
0.7548	Intermediate Similarity	NPD4965	Approved
0.7548	Intermediate Similarity	NPD4966	Approved
0.7548	Intermediate Similarity	NPD4967	Phase 2
0.7518	Intermediate Similarity	NPD5327	Phase 3
0.7517	Intermediate Similarity	NPD2796	Approved
0.7516	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7157	Approved
0.7483	Intermediate Similarity	NPD5735	Approved
0.7483	Intermediate Similarity	NPD2800	Approved
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.748	Intermediate Similarity	NPD968	Approved
0.7467	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7228	Approved
0.745	Intermediate Similarity	NPD6667	Approved
0.745	Intermediate Similarity	NPD6666	Approved
0.7448	Intermediate Similarity	NPD7033	Discontinued
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7444	Intermediate Similarity	NPD7340	Approved
0.7442	Intermediate Similarity	NPD4750	Phase 3
0.744	Intermediate Similarity	NPD846	Approved
0.744	Intermediate Similarity	NPD940	Approved
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2424	Discontinued
0.741	Intermediate Similarity	NPD2797	Approved
0.7407	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7843	Approved
0.74	Intermediate Similarity	NPD7041	Phase 2
0.74	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6583	Phase 3
0.7391	Intermediate Similarity	NPD6582	Phase 2
0.7389	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7097	Phase 1
0.7378	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2684	Approved
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7351	Intermediate Similarity	NPD2533	Approved
0.7351	Intermediate Similarity	NPD2534	Approved
0.7351	Intermediate Similarity	NPD2532	Approved
0.7347	Intermediate Similarity	NPD5762	Approved
0.7347	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD7741	Discontinued
0.7329	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4097	Suspended
0.731	Intermediate Similarity	NPD6353	Approved
0.7308	Intermediate Similarity	NPD8455	Phase 2
0.7305	Intermediate Similarity	NPD3018	Phase 2
0.7301	Intermediate Similarity	NPD5844	Phase 1
0.7292	Intermediate Similarity	NPD2238	Phase 2
0.7292	Intermediate Similarity	NPD1240	Approved
0.7292	Intermediate Similarity	NPD4140	Approved
0.729	Intermediate Similarity	NPD6072	Discontinued
0.7287	Intermediate Similarity	NPD290	Approved
0.728	Intermediate Similarity	NPD3020	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD5535	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.726	Intermediate Similarity	NPD2200	Suspended
0.725	Intermediate Similarity	NPD7199	Phase 2
0.7244	Intermediate Similarity	NPD6801	Discontinued
0.7234	Intermediate Similarity	NPD3691	Phase 2
0.7234	Intermediate Similarity	NPD3690	Phase 2
0.7229	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5126	Approved
0.7226	Intermediate Similarity	NPD5125	Phase 3
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5283	Phase 1
0.7218	Intermediate Similarity	NPD1398	Phase 1
0.7215	Intermediate Similarity	NPD3882	Suspended
0.7211	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3748	Approved
0.7208	Intermediate Similarity	NPD1653	Approved
0.72	Intermediate Similarity	NPD4535	Phase 3
0.7197	Intermediate Similarity	NPD2801	Approved
0.7192	Intermediate Similarity	NPD1607	Approved
0.7192	Intermediate Similarity	NPD2157	Approved
0.7181	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7037	Approved
0.7172	Intermediate Similarity	NPD3620	Phase 2
0.7172	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1511	Approved
0.717	Intermediate Similarity	NPD3749	Approved
0.7162	Intermediate Similarity	NPD2935	Discontinued
0.7162	Intermediate Similarity	NPD1551	Phase 2
0.7161	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7143	Intermediate Similarity	NPD7119	Phase 2
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7122	Intermediate Similarity	NPD3705	Approved
0.7111	Intermediate Similarity	NPD6387	Discontinued
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD6405	Approved
0.7103	Intermediate Similarity	NPD6407	Approved
0.7101	Intermediate Similarity	NPD6516	Phase 2
0.7101	Intermediate Similarity	NPD5846	Approved
0.7101	Intermediate Similarity	NPD4626	Approved
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.7095	Intermediate Similarity	NPD2799	Discontinued
0.7092	Intermediate Similarity	NPD3225	Approved
0.7091	Intermediate Similarity	NPD7054	Approved
0.7089	Intermediate Similarity	NPD5929	Approved
0.7089	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1242	Phase 1
0.7086	Intermediate Similarity	NPD6331	Phase 2
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD7095	Approved
0.7078	Intermediate Similarity	NPD1512	Approved
0.7078	Intermediate Similarity	NPD6090	Discontinued
0.7075	Intermediate Similarity	NPD6651	Approved
0.7073	Intermediate Similarity	NPD7473	Discontinued
0.7071	Intermediate Similarity	NPD2981	Phase 2
0.7071	Intermediate Similarity	NPD2231	Phase 2
0.7071	Intermediate Similarity	NPD2235	Phase 2
0.7071	Intermediate Similarity	NPD1608	Approved
0.7066	Intermediate Similarity	NPD7240	Approved
0.7059	Intermediate Similarity	NPD6799	Approved
0.7055	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3496	Discontinued
0.7048	Intermediate Similarity	NPD7472	Approved
0.7047	Intermediate Similarity	NPD4477	Approved
0.7047	Intermediate Similarity	NPD4476	Approved
0.7045	Intermediate Similarity	NPD5451	Approved
0.7042	Intermediate Similarity	NPD3094	Phase 2
0.704	Intermediate Similarity	NPD2859	Approved
0.704	Intermediate Similarity	NPD2860	Approved
0.7034	Intermediate Similarity	NPD1699	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