NPASS Compound

Structure

NPC77325 OpenBabel07101719142D 21 23 0 0 1 0 0 0 0 0999 V2000 0.7071 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 3.4641 1.0000 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 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 2.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 0 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 0.0000 4.0000 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 20 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 6 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 1 1 6 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.08
Volume:	279.249
LogP:	2.186
LogD:	1.74
LogS:	-3.95
# Rotatable Bonds:	1
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	3.823
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	1.8970260498463176e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.521

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	80.82218170166016%
Volume Distribution (VD):	0.498
Pgp-substrate:	18.567218780517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.805
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	12.471
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.777
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.738
Skin Sensitization:	0.315
Carcinogencity:	0.039
Eye Corrosion:	0.012
Eye Irritation:	0.24
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC77325

Natural Product ID:	NPC77325
*Common Name:**	Dehydroaltenuene B
IUPAC Name:	(3S,4aS)-3,7-dihydroxy-9-methoxy-4a-methyl-3,4-dihydrobenzo[c]chromene-2,6-dione
Synonyms:
Standard InCHIKey:	JJAKYYZRBMQHHU-WFASDCNBSA-N
Standard InCHI:	InChI=1S/C15H14O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,12,17-18H,6H2,1-2H3/t12-,15-/m0/s1
SMILES:	C[C@]12C[C@@H](C(=O)C=C1c1cc(cc(c1C(=O)O2)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482027
PubChem CID:	11616254
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32670	tubeufiaceae	Family	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643037]

☑ 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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[543675]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	20.0	mm	PMID[543675]

☑ 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 NPC77325 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	342
0.1-0.2	1499
0.2-0.3	3453
0.3-0.4	7384
0.4-0.5	10742
0.5-0.6	4234
0.6-0.7	5710
0.7-0.8	6562
0.8-0.85	2292
0.85-0.9	383
0.9-0.95	90
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4423
0.9452	High Similarity	NPC237440
0.9452	High Similarity	NPC270160
0.9441	High Similarity	NPC469542
0.9306	High Similarity	NPC472006
0.9236	High Similarity	NPC469579
0.9184	High Similarity	NPC210320
0.9184	High Similarity	NPC14098
0.9172	High Similarity	NPC51106
0.9167	High Similarity	NPC67650
0.9167	High Similarity	NPC1704
0.9161	High Similarity	NPC268052
0.9155	High Similarity	NPC135837
0.9145	High Similarity	NPC246466
0.9133	High Similarity	NPC167903
0.9122	High Similarity	NPC73411
0.9122	High Similarity	NPC215711
0.9122	High Similarity	NPC153417
0.9116	High Similarity	NPC107625
0.9103	High Similarity	NPC474385
0.9085	High Similarity	NPC235115
0.9079	High Similarity	NPC472050
0.9073	High Similarity	NPC192189
0.9067	High Similarity	NPC70016
0.9067	High Similarity	NPC215921
0.9048	High Similarity	NPC473692
0.9034	High Similarity	NPC53649
0.9034	High Similarity	NPC90411
0.9034	High Similarity	NPC244923
0.9028	High Similarity	NPC32360
0.902	High Similarity	NPC473395
0.9014	High Similarity	NPC182496
0.9014	High Similarity	NPC180905
0.9013	High Similarity	NPC99381
0.9007	High Similarity	NPC478224
0.9	High Similarity	NPC470107
0.9	High Similarity	NPC472891
0.8993	High Similarity	NPC471641
0.8993	High Similarity	NPC471642
0.8993	High Similarity	NPC240253
0.8993	High Similarity	NPC240622
0.8986	High Similarity	NPC472033
0.8986	High Similarity	NPC267509
0.8986	High Similarity	NPC260946
0.898	High Similarity	NPC86373
0.898	High Similarity	NPC280404
0.898	High Similarity	NPC210425
0.898	High Similarity	NPC277426
0.8968	High Similarity	NPC117985
0.8966	High Similarity	NPC155205
0.8961	High Similarity	NPC470339
0.8958	High Similarity	NPC472602
0.8958	High Similarity	NPC94248
0.8958	High Similarity	NPC212693
0.8958	High Similarity	NPC191835
0.8947	High Similarity	NPC281477
0.8947	High Similarity	NPC478231
0.8947	High Similarity	NPC472799
0.894	High Similarity	NPC46882
0.894	High Similarity	NPC132990
0.894	High Similarity	NPC91809
0.8933	High Similarity	NPC84142
0.8933	High Similarity	NPC198927
0.8926	High Similarity	NPC472036
0.8919	High Similarity	NPC32470
0.8919	High Similarity	NPC472034
0.8919	High Similarity	NPC316535
0.8912	High Similarity	NPC310340
0.8904	High Similarity	NPC472604
0.8904	High Similarity	NPC158634
0.8904	High Similarity	NPC472603
0.8904	High Similarity	NPC275734
0.8904	High Similarity	NPC472605
0.8904	High Similarity	NPC475730
0.8903	High Similarity	NPC472055
0.8897	High Similarity	NPC88269
0.8897	High Similarity	NPC139634
0.8897	High Similarity	NPC52358
0.8897	High Similarity	NPC105456
0.8889	High Similarity	NPC70380
0.8889	High Similarity	NPC478230
0.8889	High Similarity	NPC208173
0.8889	High Similarity	NPC82592
0.8889	High Similarity	NPC69043
0.8889	High Similarity	NPC16082
0.8889	High Similarity	NPC170189
0.8882	High Similarity	NPC470340
0.8882	High Similarity	NPC184284
0.8882	High Similarity	NPC474843
0.8882	High Similarity	NPC76041
0.8882	High Similarity	NPC115249
0.8874	High Similarity	NPC469670
0.8874	High Similarity	NPC179178
0.8874	High Similarity	NPC164762
0.8874	High Similarity	NPC469619
0.8874	High Similarity	NPC150928
0.8874	High Similarity	NPC202595
0.8873	High Similarity	NPC153783
0.8861	High Similarity	NPC20237
0.8859	High Similarity	NPC473023
0.8854	High Similarity	NPC249181
0.8851	High Similarity	NPC475201
0.8844	High Similarity	NPC250755
0.8836	High Similarity	NPC472600
0.8836	High Similarity	NPC165172
0.8836	High Similarity	NPC472601
0.8836	High Similarity	NPC469523
0.8828	High Similarity	NPC33144
0.8828	High Similarity	NPC478200
0.8824	High Similarity	NPC137301
0.8824	High Similarity	NPC155686
0.8824	High Similarity	NPC301233
0.8824	High Similarity	NPC471695
0.8816	High Similarity	NPC240768
0.8816	High Similarity	NPC200773
0.8811	High Similarity	NPC175943
0.8808	High Similarity	NPC476684
0.8805	High Similarity	NPC283041
0.88	High Similarity	NPC21835
0.8797	High Similarity	NPC191930
0.8792	High Similarity	NPC28632
0.8792	High Similarity	NPC312789
0.8792	High Similarity	NPC134621
0.8784	High Similarity	NPC471731
0.8784	High Similarity	NPC159721
0.8784	High Similarity	NPC478202
0.8784	High Similarity	NPC73028
0.8784	High Similarity	NPC471639
0.8784	High Similarity	NPC471643
0.8776	High Similarity	NPC220106
0.8776	High Similarity	NPC182421
0.8776	High Similarity	NPC313123
0.8776	High Similarity	NPC478217
0.8774	High Similarity	NPC84935
0.8774	High Similarity	NPC190020
0.8774	High Similarity	NPC472889
0.8774	High Similarity	NPC77679
0.8767	High Similarity	NPC247409
0.8767	High Similarity	NPC92655
0.8766	High Similarity	NPC317585
0.8766	High Similarity	NPC472890
0.8766	High Similarity	NPC478221
0.8766	High Similarity	NPC199926
0.8766	High Similarity	NPC237560
0.8759	High Similarity	NPC261292
0.8759	High Similarity	NPC301915
0.8758	High Similarity	NPC470338
0.8758	High Similarity	NPC271681
0.8758	High Similarity	NPC113608
0.8758	High Similarity	NPC470337
0.8758	High Similarity	NPC51824
0.8758	High Similarity	NPC268992
0.875	High Similarity	NPC27407
0.875	High Similarity	NPC142027
0.875	High Similarity	NPC56204
0.875	High Similarity	NPC119929
0.875	High Similarity	NPC475460
0.875	High Similarity	NPC295036
0.8742	High Similarity	NPC218569
0.8742	High Similarity	NPC2569
0.8742	High Similarity	NPC172329
0.8733	High Similarity	NPC237208
0.8733	High Similarity	NPC51513
0.8733	High Similarity	NPC202112
0.8732	High Similarity	NPC219892
0.8732	High Similarity	NPC189823
0.8725	High Similarity	NPC151607
0.8725	High Similarity	NPC66404
0.8725	High Similarity	NPC42540
0.8725	High Similarity	NPC95123
0.8725	High Similarity	NPC19896
0.8716	High Similarity	NPC322112
0.8716	High Similarity	NPC471733
0.8716	High Similarity	NPC105648
0.8716	High Similarity	NPC297985
0.8716	High Similarity	NPC82913
0.8716	High Similarity	NPC49108
0.871	High Similarity	NPC150227
0.871	High Similarity	NPC227062
0.8707	High Similarity	NPC156872
0.8707	High Similarity	NPC158472
0.8699	High Similarity	NPC475974
0.8693	High Similarity	NPC470569
0.8693	High Similarity	NPC72958
0.8693	High Similarity	NPC39819
0.8693	High Similarity	NPC232645
0.8693	High Similarity	NPC227166
0.869	High Similarity	NPC291454
0.869	High Similarity	NPC50455
0.869	High Similarity	NPC242712
0.8688	High Similarity	NPC473094
0.8684	High Similarity	NPC477941
0.8684	High Similarity	NPC277032
0.8675	High Similarity	NPC8817
0.8675	High Similarity	NPC259632
0.8671	High Similarity	NPC473022
0.8667	High Similarity	NPC29577
0.8667	High Similarity	NPC83272
0.8662	High Similarity	NPC243701
0.8658	High Similarity	NPC277369

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 NPC77325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	967
0.2-0.3	1749
0.3-0.4	2511
0.4-0.5	1905
0.5-0.6	1106
0.6-0.7	421
0.7-0.8	159
0.8-0.85	30
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1550	Clinical (unspecified phase)
0.8543	High Similarity	NPD2534	Approved
0.8543	High Similarity	NPD2532	Approved
0.8543	High Similarity	NPD2533	Approved
0.8514	High Similarity	NPD1549	Phase 2
0.8435	Intermediate Similarity	NPD1510	Phase 2
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3749	Approved
0.8301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1240	Approved
0.828	Intermediate Similarity	NPD1934	Approved
0.8278	Intermediate Similarity	NPD3750	Approved
0.8228	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1607	Approved
0.8165	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4380	Phase 2
0.8148	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD6799	Approved
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD3817	Phase 2
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1511	Approved
0.7988	Intermediate Similarity	NPD5711	Approved
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5710	Approved
0.7974	Intermediate Similarity	NPD2800	Approved
0.7963	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5402	Approved
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3748	Approved
0.7931	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7892	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD2801	Approved
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.787	Intermediate Similarity	NPD6797	Phase 2
0.787	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD230	Phase 1
0.7857	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7848	Intermediate Similarity	NPD5403	Approved
0.7834	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD5401	Approved
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.7811	Intermediate Similarity	NPD7074	Phase 3
0.7798	Intermediate Similarity	NPD3751	Discontinued
0.7798	Intermediate Similarity	NPD3818	Discontinued
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7751	Intermediate Similarity	NPD7054	Approved
0.775	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD1243	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD2346	Discontinued
0.7712	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD6651	Approved
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5494	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8150	Discontinued
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7566	Intermediate Similarity	NPD943	Approved
0.756	Intermediate Similarity	NPD3787	Discontinued
0.755	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD9717	Approved
0.747	Intermediate Similarity	NPD4965	Approved
0.747	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.745	Intermediate Similarity	NPD1203	Approved
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7432	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD6782	Approved
0.7432	Intermediate Similarity	NPD6780	Approved
0.7432	Intermediate Similarity	NPD6781	Approved
0.7432	Intermediate Similarity	NPD6777	Approved
0.7432	Intermediate Similarity	NPD6776	Approved
0.7432	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7403	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD447	Suspended
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD1247	Approved
0.7389	Intermediate Similarity	NPD2344	Approved
0.7381	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD1608	Approved
0.7361	Intermediate Similarity	NPD9493	Approved
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7286	Phase 2
0.7333	Intermediate Similarity	NPD1470	Approved
0.733	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD8312	Approved
0.732	Intermediate Similarity	NPD2313	Discontinued
0.732	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4287	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7312	Intermediate Similarity	NPD6190	Approved
0.7312	Intermediate Similarity	NPD7697	Approved
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3926	Phase 2
0.7305	Intermediate Similarity	NPD4288	Approved
0.7302	Intermediate Similarity	NPD8151	Discontinued
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1201	Approved
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.7283	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7874	Approved
0.7251	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5408	Approved
0.7215	Intermediate Similarity	NPD5404	Approved
0.7215	Intermediate Similarity	NPD5405	Approved
0.7215	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD2309	Approved
0.719	Intermediate Similarity	NPD4908	Phase 1
0.719	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD2654	Approved
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD1471	Phase 3
0.7168	Intermediate Similarity	NPD2403	Approved
0.7162	Intermediate Similarity	NPD17	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7105	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD5353	Approved
0.7097	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7095	Intermediate Similarity	NPD9268	Approved
0.709	Intermediate Similarity	NPD8319	Approved
0.709	Intermediate Similarity	NPD8320	Phase 1
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.7076	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7065	Intermediate Similarity	NPD4363	Phase 3
0.7065	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1019	Discontinued
0.7048	Intermediate Similarity	NPD1653	Approved
0.7047	Intermediate Similarity	NPD7783	Phase 2
0.7047	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7801	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