NPASS Compound

Structure

CID212697 OpenBabel06191716002D 21 24 0 0 1 0 0 0 0 0999 V2000 3.9971 0.7179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 1.4506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6756 1.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5135 -1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6760 -0.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3505 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6752 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 1.9349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3508 -0.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5127 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8377 1.4509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8376 1.4512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8375 0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8378 0.4837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6757 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2295 -1.4732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8098 -0.4999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3500 -0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5128 1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 9 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 8 1 1 0 0 0 12 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 1 0 0 0 15 21 1 0 0 0 0 16 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	281.835
LogP:	1.715
LogD:	1.644
LogS:	-3.802
# Rotatable Bonds:	1
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.849
Synthetic Accessibility Score:	4.097
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	3.4399374271743e-05
Pgp-inhibitor:	0.719
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.814
Plasma Protein Binding (PPB):	86.30615234375%
Volume Distribution (VD):	0.957
Pgp-substrate:	9.553890228271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.438
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.369
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.553
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.766
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.881

ADMET: Excretion

Clearance (CL):	8.383
Half-life (T1/2):	0.61

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.701
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.867
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.449
Carcinogencity:	0.9
Eye Corrosion:	0.004
Eye Irritation:	0.046
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC212697

Natural Product ID:	NPC212697
*Common Name:**	11B-Hydroxy-11B,1-Dihydromedicarpin
IUPAC Name:	(6aR,11aR,11bS)-11b-hydroxy-9-methoxy-2,6,6a,11a-tetrahydro-1H-[1]benzofuro[3,2-c]chromen-3-one
Synonyms:
Standard InCHIKey:	XIJBDLYFYFZZDS-APHBMKBZSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-19-10-2-3-11-12-8-20-14-6-9(17)4-5-16(14,18)15(12)21-13(11)7-10/h2-3,6-7,12,15,18H,4-5,8H2,1H3/t12-,15+,16+/m0/s1
SMILES:	COc1ccc2c(c1)O[C@@H]1[C@H]2COC2=CC(=O)CC[C@]12O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL391520
PubChem CID:	44437741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100000.0	nM	PMID[528184]

☑ 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 NPC212697 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	343
0.1-0.2	1244
0.2-0.3	2709
0.3-0.4	6292
0.4-0.5	11355
0.5-0.6	5069
0.6-0.7	5420
0.7-0.8	8337
0.8-0.85	1763
0.85-0.9	162
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC30720
0.8926	High Similarity	NPC472636
0.8912	High Similarity	NPC14875
0.8882	High Similarity	NPC220462
0.8867	High Similarity	NPC473996
0.8816	High Similarity	NPC164427
0.88	High Similarity	NPC471675
0.88	High Similarity	NPC471229
0.88	High Similarity	NPC472580
0.8792	High Similarity	NPC277032
0.8784	High Similarity	NPC473133
0.8784	High Similarity	NPC470670
0.8784	High Similarity	NPC47388
0.8776	High Similarity	NPC311144
0.8742	High Similarity	NPC31627
0.8742	High Similarity	NPC210597
0.8742	High Similarity	NPC476238
0.8742	High Similarity	NPC327269
0.8742	High Similarity	NPC477957
0.8733	High Similarity	NPC472421
0.8733	High Similarity	NPC267117
0.8716	High Similarity	NPC299011
0.8716	High Similarity	NPC474302
0.8707	High Similarity	NPC113770
0.8701	High Similarity	NPC125969
0.8684	High Similarity	NPC203080
0.8684	High Similarity	NPC100134
0.8684	High Similarity	NPC209760
0.8675	High Similarity	NPC471676
0.8675	High Similarity	NPC474772
0.8675	High Similarity	NPC263384
0.8675	High Similarity	NPC471677
0.8675	High Similarity	NPC244577
0.8675	High Similarity	NPC474744
0.8675	High Similarity	NPC472422
0.8675	High Similarity	NPC472423
0.8675	High Similarity	NPC472420
0.8671	High Similarity	NPC266245
0.8667	High Similarity	NPC139966
0.8667	High Similarity	NPC307052
0.8658	High Similarity	NPC91902
0.8658	High Similarity	NPC308200
0.8658	High Similarity	NPC202494
0.8658	High Similarity	NPC85773
0.8658	High Similarity	NPC472918
0.8649	High Similarity	NPC303185
0.8649	High Similarity	NPC184649
0.8649	High Similarity	NPC316535
0.8645	High Similarity	NPC472624
0.8639	High Similarity	NPC130206
0.8636	High Similarity	NPC299520
0.8636	High Similarity	NPC129684
0.8627	High Similarity	NPC175192
0.8627	High Similarity	NPC255807
0.8627	High Similarity	NPC471116
0.8627	High Similarity	NPC31018
0.8627	High Similarity	NPC476169
0.8618	High Similarity	NPC217149
0.8618	High Similarity	NPC475790
0.8618	High Similarity	NPC285623
0.8618	High Similarity	NPC216035
0.8611	High Similarity	NPC309452
0.8609	High Similarity	NPC471115
0.8609	High Similarity	NPC29777
0.8608	High Similarity	NPC173292
0.8608	High Similarity	NPC235610
0.86	High Similarity	NPC145467
0.86	High Similarity	NPC39195
0.86	High Similarity	NPC191634
0.86	High Similarity	NPC10097
0.8599	High Similarity	NPC475985
0.8599	High Similarity	NPC124038
0.859	High Similarity	NPC92589
0.8582	High Similarity	NPC162801
0.8581	High Similarity	NPC18886
0.8571	High Similarity	NPC109967
0.8571	High Similarity	NPC129053
0.8571	High Similarity	NPC469936
0.8571	High Similarity	NPC321372
0.8571	High Similarity	NPC20530
0.8571	High Similarity	NPC474738
0.8571	High Similarity	NPC78554
0.8571	High Similarity	NPC215917
0.8571	High Similarity	NPC10754
0.8571	High Similarity	NPC74397
0.8571	High Similarity	NPC475797
0.8571	High Similarity	NPC24640
0.8571	High Similarity	NPC474609
0.8562	High Similarity	NPC472583
0.8562	High Similarity	NPC60084
0.8562	High Similarity	NPC223701
0.8562	High Similarity	NPC469405
0.8562	High Similarity	NPC18727
0.8562	High Similarity	NPC7989
0.8553	High Similarity	NPC46564
0.8553	High Similarity	NPC262039
0.8553	High Similarity	NPC278476
0.8553	High Similarity	NPC319910
0.8553	High Similarity	NPC474021
0.8553	High Similarity	NPC262038
0.8553	High Similarity	NPC474023
0.8553	High Similarity	NPC476459
0.8553	High Similarity	NPC254412
0.8553	High Similarity	NPC207346
0.8552	High Similarity	NPC73078
0.8552	High Similarity	NPC148738
0.8552	High Similarity	NPC319870
0.8552	High Similarity	NPC327612
0.8544	High Similarity	NPC472277
0.8544	High Similarity	NPC300053
0.8544	High Similarity	NPC108433
0.8543	High Similarity	NPC317492
0.8543	High Similarity	NPC473016
0.8543	High Similarity	NPC472628
0.8543	High Similarity	NPC471114
0.8535	High Similarity	NPC472635
0.8535	High Similarity	NPC474162
0.8535	High Similarity	NPC472402
0.8535	High Similarity	NPC474150
0.8533	High Similarity	NPC211466
0.8533	High Similarity	NPC472627
0.8533	High Similarity	NPC176869
0.8533	High Similarity	NPC40086
0.8533	High Similarity	NPC3779
0.8533	High Similarity	NPC122828
0.8533	High Similarity	NPC476182
0.8533	High Similarity	NPC44721
0.8531	High Similarity	NPC117048
0.8531	High Similarity	NPC124085
0.8526	High Similarity	NPC328102
0.8526	High Similarity	NPC470810
0.8526	High Similarity	NPC470183
0.8523	High Similarity	NPC271288
0.8523	High Similarity	NPC131568
0.8523	High Similarity	NPC297788
0.8523	High Similarity	NPC87486
0.8523	High Similarity	NPC124780
0.8523	High Similarity	NPC131579
0.8521	High Similarity	NPC119985
0.8521	High Similarity	NPC280476
0.8516	High Similarity	NPC162869
0.8516	High Similarity	NPC474208
0.8516	High Similarity	NPC472914
0.8516	High Similarity	NPC245758
0.8516	High Similarity	NPC48208
0.8516	High Similarity	NPC27337
0.8516	High Similarity	NPC474836
0.8516	High Similarity	NPC472911
0.8516	High Similarity	NPC96167
0.8516	High Similarity	NPC475267
0.8516	High Similarity	NPC222814
0.8516	High Similarity	NPC181960
0.8516	High Similarity	NPC469584
0.8516	High Similarity	NPC472910
0.8516	High Similarity	NPC156057
0.8516	High Similarity	NPC472913
0.8514	High Similarity	NPC202981
0.8506	High Similarity	NPC67396
0.8506	High Similarity	NPC48579
0.8506	High Similarity	NPC217706
0.8506	High Similarity	NPC259710
0.8506	High Similarity	NPC304207
0.8506	High Similarity	NPC108937
0.8506	High Similarity	NPC207809
0.8506	High Similarity	NPC326910
0.8506	High Similarity	NPC477958
0.8506	High Similarity	NPC279218
0.8506	High Similarity	NPC37392
0.8506	High Similarity	NPC477530
0.8506	High Similarity	NPC267242
0.8506	High Similarity	NPC472909
0.8503	High Similarity	NPC307287
0.8503	High Similarity	NPC110228
0.8503	High Similarity	NPC284550
0.8503	High Similarity	NPC188243
0.8503	High Similarity	NPC6407
0.8503	High Similarity	NPC76445
0.8503	High Similarity	NPC129853
0.85	High Similarity	NPC288813
0.85	High Similarity	NPC152477
0.8497	Intermediate Similarity	NPC56232
0.8497	Intermediate Similarity	NPC219582
0.8497	Intermediate Similarity	NPC244583
0.8497	Intermediate Similarity	NPC302950
0.8497	Intermediate Similarity	NPC288534
0.8497	Intermediate Similarity	NPC150123
0.8497	Intermediate Similarity	NPC260979
0.8497	Intermediate Similarity	NPC10807
0.8497	Intermediate Similarity	NPC171651
0.8497	Intermediate Similarity	NPC243171
0.8497	Intermediate Similarity	NPC256141
0.8497	Intermediate Similarity	NPC35567
0.8497	Intermediate Similarity	NPC472912
0.8497	Intermediate Similarity	NPC161881
0.8497	Intermediate Similarity	NPC138288
0.8497	Intermediate Similarity	NPC275878
0.8497	Intermediate Similarity	NPC236637
0.8491	Intermediate Similarity	NPC128293
0.8491	Intermediate Similarity	NPC119589
0.8491	Intermediate Similarity	NPC170245

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 NPC212697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	781
0.2-0.3	1541
0.3-0.4	2490
0.4-0.5	2095
0.5-0.6	1134
0.6-0.7	622
0.7-0.8	172
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8497	Intermediate Similarity	NPD1934	Approved
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD5494	Approved
0.8247	Intermediate Similarity	NPD4380	Phase 2
0.8243	Intermediate Similarity	NPD1549	Phase 2
0.8217	Intermediate Similarity	NPD3882	Suspended
0.8217	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2801	Approved
0.8205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7075	Discontinued
0.8165	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6099	Approved
0.8108	Intermediate Similarity	NPD2796	Approved
0.8108	Intermediate Similarity	NPD6100	Approved
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6166	Phase 2
0.8067	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2424	Discontinued
0.7986	Intermediate Similarity	NPD4908	Phase 1
0.7974	Intermediate Similarity	NPD6799	Approved
0.7974	Intermediate Similarity	NPD1511	Approved
0.7925	Intermediate Similarity	NPD3817	Phase 2
0.7919	Intermediate Similarity	NPD1510	Phase 2
0.7911	Intermediate Similarity	NPD6801	Discontinued
0.7901	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7891	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1613	Approved
0.7879	Intermediate Similarity	NPD3751	Discontinued
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1610	Phase 2
0.7871	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD7819	Suspended
0.7848	Intermediate Similarity	NPD7411	Suspended
0.7838	Intermediate Similarity	NPD5124	Phase 1
0.7838	Intermediate Similarity	NPD6355	Discontinued
0.7838	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7054	Approved
0.7831	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7826	Intermediate Similarity	NPD3749	Approved
0.7806	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.777	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD4965	Approved
0.7764	Intermediate Similarity	NPD4967	Phase 2
0.7764	Intermediate Similarity	NPD4966	Approved
0.7762	Intermediate Similarity	NPD4749	Approved
0.7755	Intermediate Similarity	NPD3268	Approved
0.7744	Intermediate Similarity	NPD3787	Discontinued
0.774	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.7738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1652	Phase 2
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD6959	Discontinued
0.7682	Intermediate Similarity	NPD3748	Approved
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7671	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1607	Approved
0.7655	Intermediate Similarity	NPD2797	Approved
0.7651	Intermediate Similarity	NPD2403	Approved
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7808	Phase 3
0.7647	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD7229	Phase 3
0.7635	Intermediate Similarity	NPD6798	Discontinued
0.7635	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.7595	Intermediate Similarity	NPD5403	Approved
0.7595	Intermediate Similarity	NPD920	Approved
0.7593	Intermediate Similarity	NPD5402	Approved
0.7582	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6002	Phase 3
0.7582	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6005	Phase 3
0.7582	Intermediate Similarity	NPD6004	Phase 3
0.7572	Intermediate Similarity	NPD8434	Phase 2
0.7568	Intermediate Similarity	NPD3027	Phase 3
0.756	Intermediate Similarity	NPD7228	Approved
0.7551	Intermediate Similarity	NPD2861	Phase 2
0.7545	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD422	Phase 1
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD230	Phase 1
0.747	Intermediate Similarity	NPD1247	Approved
0.7468	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6233	Phase 2
0.7465	Intermediate Similarity	NPD1548	Phase 1
0.7442	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7768	Phase 2
0.7438	Intermediate Similarity	NPD1653	Approved
0.7434	Intermediate Similarity	NPD6651	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.7415	Intermediate Similarity	NPD3266	Approved
0.7389	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD7097	Phase 1
0.7379	Intermediate Similarity	NPD1091	Approved
0.7372	Intermediate Similarity	NPD1243	Approved
0.7365	Intermediate Similarity	NPD5647	Approved
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7349	Intermediate Similarity	NPD919	Approved
0.7347	Intermediate Similarity	NPD8651	Approved
0.7342	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD1608	Approved
0.7325	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.729	Intermediate Similarity	NPD1551	Phase 2
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7283	Intermediate Similarity	NPD7240	Approved
0.7278	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3225	Approved
0.7219	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5710	Approved
0.7215	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4110	Phase 3
0.7212	Intermediate Similarity	NPD5761	Phase 2
0.7212	Intermediate Similarity	NPD5760	Phase 2
0.7208	Intermediate Similarity	NPD6653	Approved
0.719	Intermediate Similarity	NPD943	Approved
0.719	Intermediate Similarity	NPD4060	Phase 1
0.7184	Intermediate Similarity	NPD7685	Pre-registration
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7171	Intermediate Similarity	NPD3764	Approved
0.7169	Intermediate Similarity	NPD5353	Approved
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7133	Intermediate Similarity	NPD7157	Approved
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4363	Phase 3
0.7127	Intermediate Similarity	NPD4360	Phase 2
0.7126	Intermediate Similarity	NPD5953	Discontinued
0.7125	Intermediate Similarity	NPD5058	Phase 3
0.7124	Intermediate Similarity	NPD4062	Phase 3
0.7123	Intermediate Similarity	NPD17	Approved
0.7122	Intermediate Similarity	NPD2684	Approved
0.7115	Intermediate Similarity	NPD4308	Phase 3
0.7115	Intermediate Similarity	NPD5588	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7286	Phase 2
0.7107	Intermediate Similarity	NPD7466	Approved
0.7105	Intermediate Similarity	NPD7095	Approved
0.7099	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5958	Discontinued
0.7086	Intermediate Similarity	NPD9494	Approved
0.7081	Intermediate Similarity	NPD2494	Approved
0.7081	Intermediate Similarity	NPD2493	Approved
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3226	Approved
0.707	Intermediate Similarity	NPD2935	Discontinued
0.7066	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD4582	Approved
0.7059	Intermediate Similarity	NPD4583	Approved
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7051	Intermediate Similarity	NPD4538	Approved
0.7051	Intermediate Similarity	NPD4536	Approved
0.7051	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD290	Approved
0.7049	Intermediate Similarity	NPD2975	Approved
0.7049	Intermediate Similarity	NPD2973	Approved
0.7049	Intermediate Similarity	NPD2974	Approved
0.7047	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7549	Discontinued
0.7042	Intermediate Similarity	NPD7843	Approved
0.7035	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7028	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