NPASS Compound

Structure

CID320789 OpenBabel06191716152D 26 30 0 0 1 0 0 0 0 0999 V2000 -5.5268 1.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5272 0.0899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1912 1.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 1.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3530 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4352 1.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6763 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0195 0.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1910 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5149 1.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5145 1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0044 0.9687 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5147 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8378 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8376 1.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6759 1.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 1.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8385 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0570 -0.0172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6757 2.9515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 2.9358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4355 0.1853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -0.0003 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 8 2 0 0 0 0 2 8 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	340.707
LogP:	4.388
LogD:	2.844
LogS:	-3.897
# Rotatable Bonds:	1
TPSA:	93.04
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	3.688
Fsp3:	0.15
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:	-4.9
MDCK Permeability:	1.591927866684273e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.53046417236328%
Volume Distribution (VD):	0.709
Pgp-substrate:	11.129387855529785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.443
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.239
CYP2D6-substrate:	0.703
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	5.677
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.786
Carcinogencity:	0.936
Eye Corrosion:	0.006
Eye Irritation:	0.793
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC320789

Natural Product ID:	NPC320789
*Common Name:**	Lachnoisoflavone B
IUPAC Name:	n.a.
Synonyms:	Lachnoisoflavone B
Standard InCHIKey:	UVJBSWKDLJKBCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O6/c1-8(2)12-6-11-14(24-12)7-15-17(18(11)22)19(23)16-10-4-3-9(21)5-13(10)25-20(16)26-15/h3-5,7,12,21-22H,1,6H2,2H3
SMILES:	CC(=C)C1CC2=C(O1)C=C3C(=C2O)C(=O)C4=C(O3)OC5=C4C=CC(=C5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689271
PubChem CID:	51041994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21265557]
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	whole plant	Dschang (west region of Cameroon)	2007-SEP	PMID[21265557]
NPO21353	Crotalaria lachnophora	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	7.0	mm	PMID[495777]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	7.3	mm	PMID[495777]

☑ 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 NPC320789 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	374
0.1-0.2	1699
0.2-0.3	3714
0.3-0.4	8785
0.4-0.5	10127
0.5-0.6	4067
0.6-0.7	5876
0.7-0.8	4915
0.8-0.85	2442
0.85-0.9	638
0.9-0.95	54
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC120220
0.9494	High Similarity	NPC260296
0.9494	High Similarity	NPC115432
0.9448	High Similarity	NPC472584
0.943	High Similarity	NPC244750
0.9427	High Similarity	NPC13879
0.9317	High Similarity	NPC155640
0.9308	High Similarity	NPC40583
0.9236	High Similarity	NPC41326
0.9177	High Similarity	NPC213608
0.9177	High Similarity	NPC1477
0.9114	High Similarity	NPC5871
0.908	High Similarity	NPC109180
0.9068	High Similarity	NPC476349
0.9068	High Similarity	NPC476350
0.9062	High Similarity	NPC160015
0.9062	High Similarity	NPC247677
0.9018	High Similarity	NPC310603
0.9006	High Similarity	NPC65504
0.9006	High Similarity	NPC260902
0.9006	High Similarity	NPC296957
0.8994	High Similarity	NPC67654
0.8963	High Similarity	NPC91288
0.8963	High Similarity	NPC38591
0.8944	High Similarity	NPC211482
0.8944	High Similarity	NPC476652
0.8938	High Similarity	NPC122365
0.8931	High Similarity	NPC156244
0.8929	High Similarity	NPC261471
0.8924	High Similarity	NPC226644
0.8924	High Similarity	NPC37226
0.8916	High Similarity	NPC476459
0.8889	High Similarity	NPC97523
0.8889	High Similarity	NPC270044
0.8889	High Similarity	NPC269495
0.8861	High Similarity	NPC135325
0.8855	High Similarity	NPC323137
0.8812	High Similarity	NPC318424
0.8812	High Similarity	NPC290671
0.8812	High Similarity	NPC170169
0.881	High Similarity	NPC477573
0.881	High Similarity	NPC78830
0.881	High Similarity	NPC218533
0.881	High Similarity	NPC477571
0.881	High Similarity	NPC477572
0.8805	High Similarity	NPC317492
0.8805	High Similarity	NPC296030
0.8805	High Similarity	NPC39929
0.8802	High Similarity	NPC86477
0.8797	High Similarity	NPC130581
0.8797	High Similarity	NPC12148
0.8795	High Similarity	NPC204088
0.8795	High Similarity	NPC259007
0.8795	High Similarity	NPC329215
0.879	High Similarity	NPC230943
0.878	High Similarity	NPC304839
0.878	High Similarity	NPC220582
0.878	High Similarity	NPC169
0.878	High Similarity	NPC114147
0.8765	High Similarity	NPC198490
0.8765	High Similarity	NPC236327
0.8765	High Similarity	NPC474542
0.8765	High Similarity	NPC148938
0.8765	High Similarity	NPC290304
0.8758	High Similarity	NPC263676
0.875	High Similarity	NPC230713
0.875	High Similarity	NPC155882
0.875	High Similarity	NPC53252
0.875	High Similarity	NPC78335
0.8743	High Similarity	NPC53640
0.8742	High Similarity	NPC39195
0.8742	High Similarity	NPC168085
0.8735	High Similarity	NPC472581
0.8735	High Similarity	NPC471286
0.8734	High Similarity	NPC210826
0.8734	High Similarity	NPC300267
0.8734	High Similarity	NPC51641
0.8727	High Similarity	NPC92589
0.8727	High Similarity	NPC45124
0.8727	High Similarity	NPC304387
0.8727	High Similarity	NPC175513
0.8727	High Similarity	NPC74854
0.8727	High Similarity	NPC30655
0.8726	High Similarity	NPC302181
0.8726	High Similarity	NPC225884
0.872	High Similarity	NPC50430
0.8713	High Similarity	NPC472661
0.8713	High Similarity	NPC164384
0.8706	High Similarity	NPC37606
0.8704	High Similarity	NPC472462
0.8704	High Similarity	NPC183874
0.8704	High Similarity	NPC235333
0.8696	High Similarity	NPC116604
0.8696	High Similarity	NPC115324
0.8696	High Similarity	NPC204561
0.8696	High Similarity	NPC317715
0.8696	High Similarity	NPC209142
0.8696	High Similarity	NPC312549
0.8696	High Similarity	NPC148945
0.8696	High Similarity	NPC309512
0.8696	High Similarity	NPC316960
0.8696	High Similarity	NPC78835
0.8688	High Similarity	NPC178202
0.8688	High Similarity	NPC37208
0.8688	High Similarity	NPC221868
0.8688	High Similarity	NPC88445
0.8683	High Similarity	NPC136641
0.8679	High Similarity	NPC17816
0.8679	High Similarity	NPC308200
0.8675	High Similarity	NPC93215
0.8671	High Similarity	NPC303185
0.8671	High Similarity	NPC184649
0.8667	High Similarity	NPC74749
0.8667	High Similarity	NPC43971
0.8667	High Similarity	NPC49009
0.8667	High Similarity	NPC19554
0.8662	High Similarity	NPC53192
0.8659	High Similarity	NPC212967
0.8659	High Similarity	NPC96342
0.8659	High Similarity	NPC246647
0.8659	High Similarity	NPC164110
0.8659	High Similarity	NPC268360
0.865	High Similarity	NPC279218
0.865	High Similarity	NPC297531
0.865	High Similarity	NPC108937
0.865	High Similarity	NPC213936
0.8647	High Similarity	NPC475964
0.8647	High Similarity	NPC157522
0.8642	High Similarity	NPC207624
0.8642	High Similarity	NPC473996
0.8639	High Similarity	NPC211309
0.8634	High Similarity	NPC191104
0.8634	High Similarity	NPC470107
0.8634	High Similarity	NPC474735
0.8634	High Similarity	NPC321896
0.8634	High Similarity	NPC476185
0.8631	High Similarity	NPC277480
0.8625	High Similarity	NPC145467
0.8625	High Similarity	NPC272194
0.8616	High Similarity	NPC299011
0.8616	High Similarity	NPC472629
0.8614	High Similarity	NPC114652
0.8614	High Similarity	NPC14822
0.8608	High Similarity	NPC68104
0.8608	High Similarity	NPC310130
0.8608	High Similarity	NPC164980
0.8608	High Similarity	NPC175504
0.8608	High Similarity	NPC75049
0.8608	High Similarity	NPC113770
0.8608	High Similarity	NPC257097
0.8608	High Similarity	NPC150408
0.8608	High Similarity	NPC169591
0.8608	High Similarity	NPC91560
0.8608	High Similarity	NPC221432
0.8608	High Similarity	NPC143896
0.8608	High Similarity	NPC39329
0.8608	High Similarity	NPC149026
0.8606	High Similarity	NPC472877
0.8605	High Similarity	NPC325176
0.8599	High Similarity	NPC4743
0.8599	High Similarity	NPC312391
0.8599	High Similarity	NPC213322
0.8599	High Similarity	NPC324386
0.8599	High Similarity	NPC3188
0.8598	High Similarity	NPC180924
0.8598	High Similarity	NPC321372
0.8598	High Similarity	NPC469936
0.8598	High Similarity	NPC470625
0.8598	High Similarity	NPC474609
0.8598	High Similarity	NPC129053
0.8598	High Similarity	NPC78554
0.8598	High Similarity	NPC109967
0.8598	High Similarity	NPC475797
0.8598	High Similarity	NPC474738
0.8596	High Similarity	NPC72455
0.858	High Similarity	NPC325429
0.858	High Similarity	NPC23668
0.858	High Similarity	NPC472580
0.858	High Similarity	NPC193976
0.858	High Similarity	NPC58668
0.858	High Similarity	NPC472636
0.858	High Similarity	NPC106372
0.8571	High Similarity	NPC19238
0.8571	High Similarity	NPC29411
0.8571	High Similarity	NPC37183
0.8571	High Similarity	NPC471114
0.8563	High Similarity	NPC193998
0.8563	High Similarity	NPC219861
0.8562	High Similarity	NPC300988
0.8562	High Similarity	NPC10990
0.8562	High Similarity	NPC304443
0.8562	High Similarity	NPC74539
0.8554	High Similarity	NPC303210
0.8554	High Similarity	NPC306978
0.8554	High Similarity	NPC95472
0.8554	High Similarity	NPC239270
0.8553	High Similarity	NPC473013
0.8553	High Similarity	NPC473015
0.8553	High Similarity	NPC271288
0.8553	High Similarity	NPC87486

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 NPC320789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	931
0.2-0.3	1712
0.3-0.4	2580
0.4-0.5	2077
0.5-0.6	1044
0.6-0.7	286
0.7-0.8	123
0.8-0.85	46
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8773	High Similarity	NPD3749	Approved
0.8596	High Similarity	NPD6559	Discontinued
0.8562	High Similarity	NPD920	Approved
0.8466	Intermediate Similarity	NPD7411	Suspended
0.8438	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8364	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD1243	Approved
0.8353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2344	Approved
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7768	Phase 2
0.8253	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.815	Intermediate Similarity	NPD3818	Discontinued
0.8137	Intermediate Similarity	NPD2309	Approved
0.8125	Intermediate Similarity	NPD2800	Approved
0.8103	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1510	Phase 2
0.8098	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD1934	Approved
0.8084	Intermediate Similarity	NPD6801	Discontinued
0.8075	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6959	Discontinued
0.805	Intermediate Similarity	NPD2796	Approved
0.8023	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD2533	Approved
0.7988	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD3750	Approved
0.7962	Intermediate Similarity	NPD1240	Approved
0.7953	Intermediate Similarity	NPD919	Approved
0.7941	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6799	Approved
0.7904	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7841	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3882	Suspended
0.7826	Intermediate Similarity	NPD1551	Phase 2
0.7821	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5953	Discontinued
0.7797	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7764	Intermediate Similarity	NPD2799	Discontinued
0.776	Intermediate Similarity	NPD4287	Approved
0.7753	Intermediate Similarity	NPD7472	Approved
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6166	Phase 2
0.7722	Intermediate Similarity	NPD2313	Discontinued
0.7719	Intermediate Similarity	NPD2801	Approved
0.7716	Intermediate Similarity	NPD2935	Discontinued
0.7711	Intermediate Similarity	NPD1511	Approved
0.7709	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD7286	Phase 2
0.7676	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3817	Phase 2
0.7669	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD7251	Discontinued
0.7657	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD3748	Approved
0.7624	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD1512	Approved
0.7616	Intermediate Similarity	NPD1465	Phase 2
0.7614	Intermediate Similarity	NPD6808	Phase 2
0.761	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5403	Approved
0.7572	Intermediate Similarity	NPD5402	Approved
0.7572	Intermediate Similarity	NPD2296	Approved
0.7568	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5401	Approved
0.7543	Intermediate Similarity	NPD6234	Discontinued
0.7542	Intermediate Similarity	NPD3751	Discontinued
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7527	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1203	Approved
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD7229	Phase 3
0.7514	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7458	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD8151	Discontinued
0.7439	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8455	Phase 2
0.7405	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3764	Approved
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7458	Discontinued
0.7384	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6832	Phase 2
0.7374	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1933	Approved
0.7356	Intermediate Similarity	NPD6279	Approved
0.7356	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD6280	Approved
0.7349	Intermediate Similarity	NPD1471	Phase 3
0.7348	Intermediate Similarity	NPD7228	Approved
0.7333	Intermediate Similarity	NPD7033	Discontinued
0.7325	Intermediate Similarity	NPD9717	Approved
0.7321	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6651	Approved
0.7286	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7783	Phase 2
0.7284	Intermediate Similarity	NPD3268	Approved
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5124	Phase 1
0.7256	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2798	Approved
0.7247	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD4363	Phase 3
0.7225	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD3787	Discontinued
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD6778	Approved
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD5761	Phase 2
0.7216	Intermediate Similarity	NPD6782	Approved
0.7216	Intermediate Similarity	NPD5760	Phase 2
0.7193	Intermediate Similarity	NPD7390	Discontinued
0.7188	Intermediate Similarity	NPD2797	Approved
0.7172	Intermediate Similarity	NPD7584	Approved
0.7157	Intermediate Similarity	NPD7870	Phase 2
0.7157	Intermediate Similarity	NPD7871	Phase 2
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7003	Approved
0.7107	Intermediate Similarity	NPD7696	Phase 3
0.7107	Intermediate Similarity	NPD7697	Approved
0.7107	Intermediate Similarity	NPD7698	Approved
0.7098	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4361	Phase 2
0.7091	Intermediate Similarity	NPD943	Approved
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD5406	Approved
0.7081	Intermediate Similarity	NPD1164	Approved
0.7081	Intermediate Similarity	NPD1729	Discontinued
0.7081	Intermediate Similarity	NPD3266	Approved
0.7081	Intermediate Similarity	NPD3267	Approved
0.7079	Intermediate Similarity	NPD4288	Approved
0.7065	Intermediate Similarity	NPD7874	Approved
0.7065	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7585	Approved
0.7037	Intermediate Similarity	NPD1019	Discontinued
0.7029	Intermediate Similarity	NPD1653	Approved
0.7019	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD9545	Approved
0.7005	Intermediate Similarity	NPD7685	Pre-registration
0.7005	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD7583	Approved
0.6988	Remote Similarity	NPD4307	Phase 2
0.6973	Remote Similarity	NPD7177	Discontinued
0.697	Remote Similarity	NPD411	Approved
0.697	Remote Similarity	NPD6798	Discontinued
0.6965	Remote Similarity	NPD7701	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