NPASS Compound

Structure

NPC73320 OpenBabel07101718322D 21 24 0 0 1 0 0 0 0 0999 V2000 -2.6831 1.6910 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 0.4067 -2.5316 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 -3.5491 0.1910 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 -1.8171 -1.8090 0.0000 C 0 0 0 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 0.0000 -1.6180 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 1.5823 -0.9135 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 1.9890 -1.8271 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 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1646 -0.2091 0.0000 O 0 0 0 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 -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 2 2 0 0 0 0 1 8 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 14 2 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 7 1 6 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 10 1 6 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	276.562
LogP:	3.071
LogD:	2.373
LogS:	-4.48
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	3.597
Fsp3:	0.188
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:	-4.881
MDCK Permeability:	8.085239642241504e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.638
30% Bioavailability (F30%):	0.386

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	97.32904052734375%
Volume Distribution (VD):	0.594
Pgp-substrate:	2.053982734680176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.514
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	3.915
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.88
Carcinogencity:	0.793
Eye Corrosion:	0.004
Eye Irritation:	0.899
Respiratory Toxicity:	0.47

Download Data

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

Natural Product: NPC73320

Natural Product ID:	NPC73320
*Common Name:**	Erythribyssin B
IUPAC Name:	(6aR,11aR)-3,9-dihydroxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-10-carbaldehyde
Synonyms:
Standard InCHIKey:	FJZRCLCBDONNNU-LRDDRELGSA-N
Standard InCHI:	InChI=1S/C16H12O5/c17-6-11-13(19)4-3-9-12-7-20-14-5-8(18)1-2-10(14)16(12)21-15(9)11/h1-6,12,16,18-19H,7H2/t12-,16-/m0/s1
SMILES:	c1cc2c(cc1O)OC[C@H]1c3ccc(c(C=O)c3O[C@@H]21)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079406
PubChem CID:	46879997
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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	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	5

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[453901]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[453901]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[453901]

☑ 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 NPC73320 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	386
0.1-0.2	1596
0.2-0.3	3770
0.3-0.4	10118
0.4-0.5	8338
0.5-0.6	3662
0.6-0.7	5830
0.7-0.8	6338
0.8-0.85	1752
0.85-0.9	753
0.9-0.95	153
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC308200
0.9236	High Similarity	NPC271288
0.9184	High Similarity	NPC321896
0.9184	High Similarity	NPC476185
0.9178	High Similarity	NPC39195
0.9178	High Similarity	NPC145467
0.9178	High Similarity	NPC168085
0.9172	High Similarity	NPC472629
0.9167	High Similarity	NPC113770
0.9167	High Similarity	NPC85162
0.9167	High Similarity	NPC77794
0.9167	High Similarity	NPC81697
0.9167	High Similarity	NPC278249
0.9167	High Similarity	NPC107177
0.9167	High Similarity	NPC125894
0.9167	High Similarity	NPC471621
0.9167	High Similarity	NPC223812
0.9161	High Similarity	NPC213322
0.9161	High Similarity	NPC312391
0.9161	High Similarity	NPC4743
0.9161	High Similarity	NPC324386
0.9155	High Similarity	NPC316480
0.9128	High Similarity	NPC122365
0.9122	High Similarity	NPC472636
0.9116	High Similarity	NPC471114
0.9116	High Similarity	NPC317492
0.9116	High Similarity	NPC473016
0.911	High Similarity	NPC10990
0.911	High Similarity	NPC300988
0.9103	High Similarity	NPC473015
0.9103	High Similarity	NPC124780
0.9103	High Similarity	NPC473014
0.9103	High Similarity	NPC271590
0.9103	High Similarity	NPC311144
0.9103	High Similarity	NPC110776
0.9103	High Similarity	NPC303185
0.9103	High Similarity	NPC87486
0.9103	High Similarity	NPC184649
0.9103	High Similarity	NPC235217
0.9103	High Similarity	NPC131579
0.9103	High Similarity	NPC470890
0.9103	High Similarity	NPC473013
0.9103	High Similarity	NPC131568
0.9097	High Similarity	NPC64915
0.9097	High Similarity	NPC148757
0.9097	High Similarity	NPC166934
0.9097	High Similarity	NPC1089
0.9097	High Similarity	NPC125855
0.9097	High Similarity	NPC324134
0.9097	High Similarity	NPC306829
0.9097	High Similarity	NPC167624
0.9097	High Similarity	NPC10937
0.9097	High Similarity	NPC107572
0.9097	High Similarity	NPC76338
0.9097	High Similarity	NPC76372
0.9097	High Similarity	NPC161506
0.9097	High Similarity	NPC32739
0.9097	High Similarity	NPC227579
0.9097	High Similarity	NPC37496
0.9097	High Similarity	NPC78
0.9097	High Similarity	NPC166482
0.9097	High Similarity	NPC194432
0.9097	High Similarity	NPC223500
0.9097	High Similarity	NPC265040
0.9097	High Similarity	NPC177354
0.9097	High Similarity	NPC220998
0.9097	High Similarity	NPC324436
0.9097	High Similarity	NPC328164
0.9097	High Similarity	NPC66515
0.9097	High Similarity	NPC40833
0.9097	High Similarity	NPC202981
0.9097	High Similarity	NPC228504
0.9097	High Similarity	NPC182852
0.9097	High Similarity	NPC296917
0.9085	High Similarity	NPC118813
0.906	High Similarity	NPC473996
0.9054	High Similarity	NPC29777
0.9054	High Similarity	NPC471115
0.9041	High Similarity	NPC299011
0.9041	High Similarity	NPC2416
0.9041	High Similarity	NPC127059
0.9041	High Similarity	NPC285630
0.9041	High Similarity	NPC476153
0.9041	High Similarity	NPC290133
0.9041	High Similarity	NPC24136
0.9041	High Similarity	NPC187282
0.9041	High Similarity	NPC215885
0.9041	High Similarity	NPC477955
0.9034	High Similarity	NPC150408
0.9034	High Similarity	NPC185276
0.9034	High Similarity	NPC149026
0.9034	High Similarity	NPC39329
0.9034	High Similarity	NPC143896
0.9034	High Similarity	NPC214166
0.9034	High Similarity	NPC164980
0.9034	High Similarity	NPC310130
0.9034	High Similarity	NPC91560
0.9034	High Similarity	NPC316816
0.9034	High Similarity	NPC257097
0.9034	High Similarity	NPC75049
0.9034	High Similarity	NPC169591
0.9034	High Similarity	NPC68104
0.9034	High Similarity	NPC478086
0.9034	High Similarity	NPC175504
0.9034	High Similarity	NPC221432
0.9028	High Similarity	NPC96408
0.9028	High Similarity	NPC17170
0.9028	High Similarity	NPC279650
0.9028	High Similarity	NPC156190
0.9028	High Similarity	NPC248372
0.9028	High Similarity	NPC166689
0.9028	High Similarity	NPC3188
0.9028	High Similarity	NPC258630
0.9028	High Similarity	NPC110038
0.9021	High Similarity	NPC20709
0.9021	High Similarity	NPC261234
0.9021	High Similarity	NPC310135
0.9021	High Similarity	NPC222342
0.9021	High Similarity	NPC150648
0.9021	High Similarity	NPC265871
0.9021	High Similarity	NPC225153
0.9021	High Similarity	NPC329203
0.9021	High Similarity	NPC274784
0.9014	High Similarity	NPC287246
0.9014	High Similarity	NPC296490
0.9014	High Similarity	NPC13768
0.9014	High Similarity	NPC32441
0.9014	High Similarity	NPC295261
0.9014	High Similarity	NPC79943
0.9014	High Similarity	NPC107586
0.9014	High Similarity	NPC12296
0.9014	High Similarity	NPC243083
0.9013	High Similarity	NPC40583
0.9007	High Similarity	NPC476652
0.9007	High Similarity	NPC211482
0.9	High Similarity	NPC213608
0.9	High Similarity	NPC1477
0.8993	High Similarity	NPC471675
0.8993	High Similarity	NPC148945
0.8993	High Similarity	NPC178484
0.8993	High Similarity	NPC290671
0.8993	High Similarity	NPC78835
0.8993	High Similarity	NPC204561
0.8993	High Similarity	NPC309512
0.8993	High Similarity	NPC472580
0.8993	High Similarity	NPC317715
0.8993	High Similarity	NPC316960
0.8986	High Similarity	NPC214493
0.898	High Similarity	NPC296998
0.898	High Similarity	NPC473077
0.8973	High Similarity	NPC470135
0.8973	High Similarity	NPC197252
0.8973	High Similarity	NPC209040
0.8973	High Similarity	NPC224714
0.8973	High Similarity	NPC470136
0.8973	High Similarity	NPC236766
0.8973	High Similarity	NPC39045
0.8966	High Similarity	NPC73028
0.8958	High Similarity	NPC6407
0.8958	High Similarity	NPC284550
0.8958	High Similarity	NPC110228
0.8958	High Similarity	NPC76445
0.8958	High Similarity	NPC129853
0.8958	High Similarity	NPC188243
0.8958	High Similarity	NPC182421
0.8951	High Similarity	NPC472460
0.8951	High Similarity	NPC329225
0.8951	High Similarity	NPC147686
0.8933	High Similarity	NPC217149
0.8933	High Similarity	NPC476238
0.8933	High Similarity	NPC477957
0.8933	High Similarity	NPC31627
0.8933	High Similarity	NPC5871
0.8933	High Similarity	NPC327269
0.8933	High Similarity	NPC216035
0.8926	High Similarity	NPC472633
0.8926	High Similarity	NPC472421
0.8912	High Similarity	NPC470132
0.8912	High Similarity	NPC474161
0.8912	High Similarity	NPC475052
0.8912	High Similarity	NPC111786
0.8912	High Similarity	NPC473078
0.8912	High Similarity	NPC301276
0.8912	High Similarity	NPC214774
0.8912	High Similarity	NPC470134
0.8912	High Similarity	NPC470133
0.8912	High Similarity	NPC176229
0.8912	High Similarity	NPC88964
0.8912	High Similarity	NPC312973
0.8912	High Similarity	NPC109183
0.8912	High Similarity	NPC54577
0.8912	High Similarity	NPC246948
0.8912	High Similarity	NPC470131
0.8912	High Similarity	NPC476088
0.8912	High Similarity	NPC83357
0.8912	High Similarity	NPC195621
0.8912	High Similarity	NPC470647
0.8912	High Similarity	NPC267375
0.8912	High Similarity	NPC20488
0.8912	High Similarity	NPC67805

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 NPC73320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	927
0.2-0.3	1526
0.3-0.4	2608
0.4-0.5	1900
0.5-0.6	1194
0.6-0.7	462
0.7-0.8	150
0.8-0.85	29
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9014	High Similarity	NPD1552	Clinical (unspecified phase)
0.9014	High Similarity	NPD1550	Clinical (unspecified phase)
0.8951	High Similarity	NPD1549	Phase 2
0.8844	High Similarity	NPD4378	Clinical (unspecified phase)
0.8816	High Similarity	NPD8443	Clinical (unspecified phase)
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8675	High Similarity	NPD4380	Phase 2
0.8611	High Similarity	NPD1510	Phase 2
0.8562	High Similarity	NPD1934	Approved
0.8552	High Similarity	NPD1551	Phase 2
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8425	Intermediate Similarity	NPD2796	Approved
0.8405	Intermediate Similarity	NPD6559	Discontinued
0.8397	Intermediate Similarity	NPD7768	Phase 2
0.8387	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7819	Suspended
0.8378	Intermediate Similarity	NPD2800	Approved
0.8377	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD5494	Approved
0.8344	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD3750	Approved
0.8302	Intermediate Similarity	NPD6959	Discontinued
0.8278	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD920	Approved
0.8228	Intermediate Similarity	NPD3749	Approved
0.8224	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1607	Approved
0.8212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD1610	Phase 2
0.8194	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1512	Approved
0.8148	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2534	Approved
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4908	Phase 1
0.8054	Intermediate Similarity	NPD2935	Discontinued
0.805	Intermediate Similarity	NPD3882	Suspended
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8038	Intermediate Similarity	NPD2801	Approved
0.8037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD3748	Approved
0.7945	Intermediate Similarity	NPD2313	Discontinued
0.7943	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6799	Approved
0.7895	Intermediate Similarity	NPD1243	Approved
0.7895	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5403	Approved
0.7881	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2344	Approved
0.7871	Intermediate Similarity	NPD5401	Approved
0.7848	Intermediate Similarity	NPD6599	Discontinued
0.7847	Intermediate Similarity	NPD1203	Approved
0.7844	Intermediate Similarity	NPD7074	Phase 3
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7799	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7764	Intermediate Similarity	NPD5402	Approved
0.7763	Intermediate Similarity	NPD2346	Discontinued
0.7744	Intermediate Similarity	NPD1247	Approved
0.774	Intermediate Similarity	NPD2861	Phase 2
0.7738	Intermediate Similarity	NPD7472	Approved
0.7733	Intermediate Similarity	NPD6651	Approved
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7677	Intermediate Similarity	NPD2309	Approved
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3226	Approved
0.767	Intermediate Similarity	NPD4363	Phase 3
0.767	Intermediate Similarity	NPD4360	Phase 2
0.7667	Intermediate Similarity	NPD5124	Phase 1
0.7667	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.7603	Intermediate Similarity	NPD2797	Approved
0.7602	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD5710	Approved
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD3764	Approved
0.7582	Intermediate Similarity	NPD6100	Approved
0.7582	Intermediate Similarity	NPD6099	Approved
0.7574	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7568	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2798	Approved
0.7532	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6005	Phase 3
0.7532	Intermediate Similarity	NPD6004	Phase 3
0.7532	Intermediate Similarity	NPD6002	Phase 3
0.7532	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4361	Phase 2
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5760	Phase 2
0.7485	Intermediate Similarity	NPD5761	Phase 2
0.7467	Intermediate Similarity	NPD3268	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7448	Intermediate Similarity	NPD422	Phase 1
0.7439	Intermediate Similarity	NPD4288	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7423	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD6234	Discontinued
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4965	Approved
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD943	Approved
0.7365	Intermediate Similarity	NPD1164	Approved
0.7358	Intermediate Similarity	NPD7390	Discontinued
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1201	Approved
0.732	Intermediate Similarity	NPD1933	Approved
0.7297	Intermediate Similarity	NPD3225	Approved
0.7279	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7261	Intermediate Similarity	NPD2424	Discontinued
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD1470	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7247	Intermediate Similarity	NPD4287	Approved
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD5405	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD1729	Discontinued
0.7219	Intermediate Similarity	NPD7199	Phase 2
0.7215	Intermediate Similarity	NPD2654	Approved
0.7209	Intermediate Similarity	NPD7228	Approved
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7208	Intermediate Similarity	NPD447	Suspended
0.7205	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1019	Discontinued
0.7181	Intermediate Similarity	NPD1876	Approved
0.7171	Intermediate Similarity	NPD3027	Phase 3
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1481	Phase 2
0.7153	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD4476	Approved
0.7126	Intermediate Similarity	NPD2296	Approved
0.7124	Intermediate Similarity	NPD411	Approved
0.7124	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1652	Phase 2
0.7104	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD1535	Discovery
0.7093	Intermediate Similarity	NPD2403	Approved
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7075	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD5588	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data