NPASS Compound

Structure

NPC301233 OpenBabel07101719132D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7522 -0.6753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3186 0.1489 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 1.7321 3.0000 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 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 -0.7934 -0.3912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7098 0.9422 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9938 1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7672 0.6084 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 2 3 1 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 2 1 6 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 1 0 0 0 14 20 1 0 0 0 0 15 1 1 1 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.09
Volume:	290.676
LogP:	0.889
LogD:	0.19
LogS:	-3.82
# Rotatable Bonds:	2
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	4.31
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.45
MDCK Permeability:	6.783969001844525e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.855
Human Intestinal Absorption (HIA):	0.649
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.758

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	60.803043365478516%
Volume Distribution (VD):	0.873
Pgp-substrate:	45.87739562988281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.129
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.428
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	6.524
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.623
Drug-inuced Liver Injury (DILI):	0.094
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.272
Skin Sensitization:	0.047
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.325

Download Data

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

Natural Product: NPC301233

Natural Product ID:	NPC301233
*Common Name:**	Lachnone D
IUPAC Name:	(2R,3S)-3,5-dihydroxy-7-(hydroxymethyl)-2-methyl-2-[(2S)-5-oxooxolan-2-yl]-3H-chromen-4-one
Synonyms:	Lachnone D
Standard InCHIKey:	PAPGAOZQPFDLRG-VQISRLSMSA-N
Standard InCHI:	InChI=1S/C15H16O7/c1-15(10-2-3-11(18)21-10)14(20)13(19)12-8(17)4-7(6-16)5-9(12)22-15/h4-5,10,14,16-17,20H,2-3,6H2,1H3/t10-,14+,15-/m0/s1
SMILES:	C[C@]1([C@@H]2CCC(=O)O2)[C@@H](C(=O)c2c(cc(cc2O1)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496848
PubChem CID:	11616513
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
NPO32596	lachnum sp. bcc 2424	Species	Hyaloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792425]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	200.0	ug.mL-1	PMID[544256]

☑ 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 NPC301233 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	332
0.1-0.2	1358
0.2-0.3	3272
0.3-0.4	7551
0.4-0.5	10575
0.5-0.6	4876
0.6-0.7	5596
0.7-0.8	7196
0.8-0.85	1759
0.85-0.9	175
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC316535
0.915	High Similarity	NPC326910
0.915	High Similarity	NPC237560
0.9145	High Similarity	NPC253904
0.9145	High Similarity	NPC321363
0.9139	High Similarity	NPC475717
0.9103	High Similarity	NPC117985
0.9091	High Similarity	NPC154341
0.9091	High Similarity	NPC272550
0.9026	High Similarity	NPC175192
0.894	High Similarity	NPC202494
0.894	High Similarity	NPC21835
0.8912	High Similarity	NPC268691
0.891	High Similarity	NPC473395
0.8896	High Similarity	NPC256141
0.8889	High Similarity	NPC179178
0.8889	High Similarity	NPC116822
0.8882	High Similarity	NPC191634
0.8882	High Similarity	NPC218569
0.8868	High Similarity	NPC477677
0.8868	High Similarity	NPC264756
0.8868	High Similarity	NPC34910
0.8844	High Similarity	NPC287068
0.8831	High Similarity	NPC200773
0.8831	High Similarity	NPC215921
0.8831	High Similarity	NPC240768
0.8831	High Similarity	NPC70016
0.8824	High Similarity	NPC237440
0.8824	High Similarity	NPC270160
0.8824	High Similarity	NPC4423
0.8824	High Similarity	NPC77325
0.8816	High Similarity	NPC47388
0.8816	High Similarity	NPC470670
0.8816	High Similarity	NPC91902
0.8816	High Similarity	NPC473133
0.8816	High Similarity	NPC85773
0.8808	High Similarity	NPC297788
0.8797	High Similarity	NPC470810
0.879	High Similarity	NPC190020
0.879	High Similarity	NPC84935
0.879	High Similarity	NPC246466
0.879	High Similarity	NPC77679
0.8782	High Similarity	NPC199926
0.8774	High Similarity	NPC275878
0.8774	High Similarity	NPC271681
0.8766	High Similarity	NPC470908
0.8766	High Similarity	NPC180351
0.8758	High Similarity	NPC228012
0.8742	High Similarity	NPC112418
0.8742	High Similarity	NPC45124
0.8742	High Similarity	NPC74854
0.8742	High Similarity	NPC30655
0.8734	High Similarity	NPC470339
0.8733	High Similarity	NPC150023
0.8727	High Similarity	NPC324220
0.8727	High Similarity	NPC312630
0.8726	High Similarity	NPC164427
0.8726	High Similarity	NPC313922
0.8726	High Similarity	NPC150227
0.8718	High Similarity	NPC281477
0.8718	High Similarity	NPC198236
0.8718	High Similarity	NPC470331
0.871	High Similarity	NPC474772
0.871	High Similarity	NPC262039
0.871	High Similarity	NPC254412
0.871	High Similarity	NPC319910
0.871	High Similarity	NPC278476
0.871	High Similarity	NPC46564
0.871	High Similarity	NPC472423
0.871	High Similarity	NPC207346
0.871	High Similarity	NPC262038
0.871	High Similarity	NPC472636
0.871	High Similarity	NPC471229
0.871	High Similarity	NPC474744
0.871	High Similarity	NPC295650
0.8704	High Similarity	NPC473094
0.8701	High Similarity	NPC477941
0.8701	High Similarity	NPC277032
0.8693	High Similarity	NPC211466
0.8693	High Similarity	NPC122828
0.8693	High Similarity	NPC40086
0.8693	High Similarity	NPC44721
0.8693	High Similarity	NPC210320
0.8693	High Similarity	NPC53362
0.8693	High Similarity	NPC472918
0.8693	High Similarity	NPC3779
0.8693	High Similarity	NPC166583
0.8693	High Similarity	NPC176869
0.8693	High Similarity	NPC476182
0.8688	High Similarity	NPC471745
0.8684	High Similarity	NPC4152
0.8684	High Similarity	NPC279417
0.8684	High Similarity	NPC62290
0.8684	High Similarity	NPC326506
0.8684	High Similarity	NPC142731
0.8684	High Similarity	NPC306607
0.8684	High Similarity	NPC49130
0.8684	High Similarity	NPC208176
0.8679	High Similarity	NPC284918
0.8679	High Similarity	NPC472055
0.8679	High Similarity	NPC470183
0.8679	High Similarity	NPC471744
0.8675	High Similarity	NPC476310
0.8675	High Similarity	NPC476164
0.8675	High Similarity	NPC469542
0.8671	High Similarity	NPC282390
0.8671	High Similarity	NPC281137
0.8671	High Similarity	NPC477833
0.8671	High Similarity	NPC476930
0.8662	High Similarity	NPC304207
0.8662	High Similarity	NPC473241
0.8662	High Similarity	NPC217706
0.8662	High Similarity	NPC16082
0.8662	High Similarity	NPC259710
0.8662	High Similarity	NPC99381
0.8662	High Similarity	NPC79998
0.8662	High Similarity	NPC82592
0.8662	High Similarity	NPC48579
0.8662	High Similarity	NPC279218
0.8662	High Similarity	NPC108937
0.8662	High Similarity	NPC207809
0.8654	High Similarity	NPC473996
0.8654	High Similarity	NPC36835
0.8654	High Similarity	NPC171651
0.8654	High Similarity	NPC217149
0.8654	High Similarity	NPC216035
0.8654	High Similarity	NPC243171
0.8654	High Similarity	NPC240476
0.8654	High Similarity	NPC246162
0.8654	High Similarity	NPC19721
0.8654	High Similarity	NPC138288
0.8654	High Similarity	NPC167903
0.8654	High Similarity	NPC260491
0.8654	High Similarity	NPC35567
0.8654	High Similarity	NPC61506
0.8654	High Similarity	NPC9743
0.8654	High Similarity	NPC210597
0.865	High Similarity	NPC473095
0.865	High Similarity	NPC473096
0.8645	High Similarity	NPC267117
0.8645	High Similarity	NPC327059
0.8645	High Similarity	NPC321387
0.8645	High Similarity	NPC105136
0.8645	High Similarity	NPC472421
0.8636	High Similarity	NPC10097
0.8636	High Similarity	NPC215711
0.8636	High Similarity	NPC73411
0.8634	High Similarity	NPC124038
0.8631	High Similarity	NPC475656
0.8631	High Similarity	NPC475148
0.8627	High Similarity	NPC474302
0.8627	High Similarity	NPC1940
0.8627	High Similarity	NPC148011
0.8627	High Similarity	NPC260946
0.8618	High Similarity	NPC10302
0.8618	High Similarity	NPC105381
0.8618	High Similarity	NPC18886
0.8616	High Similarity	NPC22192
0.8616	High Similarity	NPC152904
0.8616	High Similarity	NPC279732
0.8616	High Similarity	NPC470607
0.8609	High Similarity	NPC74397
0.8609	High Similarity	NPC171870
0.8608	High Similarity	NPC321372
0.8608	High Similarity	NPC129053
0.8608	High Similarity	NPC472050
0.8608	High Similarity	NPC474609
0.8608	High Similarity	NPC326037
0.8608	High Similarity	NPC10754
0.8608	High Similarity	NPC471500
0.8608	High Similarity	NPC215917
0.8608	High Similarity	NPC250922
0.8608	High Similarity	NPC78554
0.8608	High Similarity	NPC13858
0.8608	High Similarity	NPC475797
0.8608	High Similarity	NPC109967
0.8608	High Similarity	NPC469936
0.8608	High Similarity	NPC201837
0.8608	High Similarity	NPC20530
0.8608	High Similarity	NPC320825
0.8608	High Similarity	NPC474738
0.8599	High Similarity	NPC325028
0.8599	High Similarity	NPC246328
0.8599	High Similarity	NPC248793
0.8599	High Similarity	NPC469405
0.8599	High Similarity	NPC180301
0.8599	High Similarity	NPC293286
0.8599	High Similarity	NPC193200
0.8599	High Similarity	NPC209760
0.8599	High Similarity	NPC203080
0.8599	High Similarity	NPC27532
0.8599	High Similarity	NPC478231
0.8599	High Similarity	NPC100134
0.8599	High Similarity	NPC256346
0.8598	High Similarity	NPC315306
0.8598	High Similarity	NPC313717
0.8591	High Similarity	NPC98395
0.859	High Similarity	NPC474021
0.859	High Similarity	NPC471675
0.859	High Similarity	NPC39819

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 NPC301233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	837
0.2-0.3	1887
0.3-0.4	2516
0.4-0.5	1978
0.5-0.6	1058
0.6-0.7	396
0.7-0.8	159
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2532	Approved
0.8442	Intermediate Similarity	NPD2534	Approved
0.8442	Intermediate Similarity	NPD2533	Approved
0.8428	Intermediate Similarity	NPD5402	Approved
0.8418	Intermediate Similarity	NPD1934	Approved
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8377	Intermediate Similarity	NPD6799	Approved
0.8365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8302	Intermediate Similarity	NPD6801	Discontinued
0.8274	Intermediate Similarity	NPD6559	Discontinued
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD3818	Discontinued
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5403	Approved
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.817	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1549	Phase 2
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8153	Intermediate Similarity	NPD1512	Approved
0.8137	Intermediate Similarity	NPD2801	Approved
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5401	Approved
0.8059	Intermediate Similarity	NPD7251	Discontinued
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD7054	Approved
0.7961	Intermediate Similarity	NPD1607	Approved
0.7955	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4628	Phase 3
0.7949	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7472	Approved
0.7939	Intermediate Similarity	NPD919	Approved
0.7904	Intermediate Similarity	NPD5710	Approved
0.7904	Intermediate Similarity	NPD5711	Approved
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD5494	Approved
0.7885	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7879	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD920	Approved
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD1510	Phase 2
0.7829	Intermediate Similarity	NPD1240	Approved
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD6099	Approved
0.7806	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD447	Suspended
0.7778	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD1243	Approved
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1247	Approved
0.7727	Intermediate Similarity	NPD8434	Phase 2
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7669	Intermediate Similarity	NPD3226	Approved
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7033	Discontinued
0.7627	Intermediate Similarity	NPD8150	Discontinued
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.7602	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3787	Discontinued
0.7582	Intermediate Similarity	NPD411	Approved
0.7582	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7544	Intermediate Similarity	NPD3926	Phase 2
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7517	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD1203	Approved
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6779	Approved
0.7459	Intermediate Similarity	NPD6782	Approved
0.7459	Intermediate Similarity	NPD6777	Approved
0.7459	Intermediate Similarity	NPD6778	Approved
0.7459	Intermediate Similarity	NPD6776	Approved
0.7459	Intermediate Similarity	NPD6781	Approved
0.7459	Intermediate Similarity	NPD6780	Approved
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD37	Approved
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7399	Intermediate Similarity	NPD2403	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7396	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7372	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD943	Approved
0.7372	Intermediate Similarity	NPD1613	Approved
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4749	Approved
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6190	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1778	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7312	Intermediate Similarity	NPD2344	Approved
0.731	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7296	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1653	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD6651	Approved
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7249	Intermediate Similarity	NPD7698	Approved
0.7249	Intermediate Similarity	NPD7696	Phase 3
0.7249	Intermediate Similarity	NPD7697	Approved
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD7870	Phase 2
0.7211	Intermediate Similarity	NPD7871	Phase 2
0.7208	Intermediate Similarity	NPD1019	Discontinued
0.7208	Intermediate Similarity	NPD5647	Approved
0.7207	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5762	Approved
0.7205	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6004	Phase 3
0.7205	Intermediate Similarity	NPD5763	Approved
0.7205	Intermediate Similarity	NPD6002	Phase 3
0.7205	Intermediate Similarity	NPD6005	Phase 3
0.7189	Intermediate Similarity	NPD6534	Approved
0.7189	Intermediate Similarity	NPD6535	Approved
0.7188	Intermediate Similarity	NPD7701	Phase 2
0.7188	Intermediate Similarity	NPD3748	Approved
0.7165	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7783	Phase 2
0.7162	Intermediate Similarity	NPD9493	Approved
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.7117	Intermediate Similarity	NPD2654	Approved
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1933	Approved
0.7105	Intermediate Similarity	NPD1091	Approved
0.7102	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7086	Intermediate Similarity	NPD17	Approved
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7077	Intermediate Similarity	NPD7801	Approved
0.7076	Intermediate Similarity	NPD5761	Phase 2
0.7076	Intermediate Similarity	NPD5760	Phase 2
0.7074	Intermediate Similarity	NPD7700	Phase 2
0.7074	Intermediate Similarity	NPD7699	Phase 2
0.707	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD3027	Phase 3
0.7067	Intermediate Similarity	NPD9545	Approved
0.7063	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7056	Intermediate Similarity	NPD7685	Pre-registration
0.7048	Intermediate Similarity	NPD7390	Discontinued

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