NPASS Compound

Structure

NPC5990 OpenBabel07101719142D 28 30 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 2.5981 0.5000 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 0.0000 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 -3.4641 2.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 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 -1.7321 0.0000 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 -0.8660 1.5000 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 -1.7321 2.0000 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 0.8660 0.5000 0.0000 C 0 0 1 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 -2.5981 -1.5000 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 -1.7321 3.0000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 23 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 24 2 0 0 0 0 11 17 1 0 0 0 0 11 25 2 0 0 0 0 14 13 1 6 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 1 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 5 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	221.11
Volume:	219.897
LogP:	1.725
LogD:	1.459
LogS:	-1.63
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.533
Fsp3:	0.5
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:	-4.48
MDCK Permeability:	2.927320201706607e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	28.085865020751953%
Volume Distribution (VD):	2.468
Pgp-substrate:	47.16450500488281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.124
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.278
CYP3A4-substrate:	0.827

ADMET: Excretion

Clearance (CL):	13.79
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.48
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.642
Carcinogencity:	0.833
Eye Corrosion:	0.013
Eye Irritation:	0.018
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC5990

Natural Product ID:	NPC5990
*Common Name:**	Euglobal Ia2
IUPAC Name:	(7R,8aR,9S,10aR)-1,3-dihydroxy-10a-methyl-9-(2-methylpropyl)-7-propan-2-yl-7,8,8a,9-tetrahydroxanthene-2,4-dicarbaldehyde
Synonyms:	Euglobal IA2
Standard InCHIKey:	GCAXPYWXIWWHHT-UVJWIIJLSA-N
Standard InCHI:	InChI=1S/C23H30O5/c1-12(2)8-15-18-9-14(13(3)4)6-7-23(18,5)28-22-17(11-25)20(26)16(10-24)21(27)19(15)22/h6-7,10-15,18,26-27H,8-9H2,1-5H3/t14-,15+,18-,23-/m1/s1
SMILES:	O=Cc1c(O)c(C=O)c2c(c1O)[C@@H](CC(C)C)[C@@H]1[C@@](O2)(C)C=C[C@H](C1)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454049
PubChem CID:	44558994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO19242	Eucalyptus albens	Species	Myrtaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3953	Individual Protein	Plasminogen activator inhibitor-1	Homo sapiens	IC50	=	138000.0	nM	PMID[528116]

☑ 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 NPC5990 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	364
0.1-0.2	1482
0.2-0.3	3460
0.3-0.4	8635
0.4-0.5	10639
0.5-0.6	4167
0.6-0.7	6772
0.7-0.8	5144
0.8-0.85	1407
0.85-0.9	584
0.9-0.95	38
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC82534
0.9291	High Similarity	NPC285659
0.9291	High Similarity	NPC81337
0.9291	High Similarity	NPC157497
0.9231	High Similarity	NPC271288
0.9167	High Similarity	NPC477955
0.9167	High Similarity	NPC2416
0.9167	High Similarity	NPC476153
0.9167	High Similarity	NPC215885
0.9161	High Similarity	NPC471621
0.9137	High Similarity	NPC101752
0.911	High Similarity	NPC214493
0.911	High Similarity	NPC473016
0.9103	High Similarity	NPC474108
0.9103	High Similarity	NPC308200
0.9103	High Similarity	NPC177995
0.9103	High Similarity	NPC245757
0.9103	High Similarity	NPC304351
0.9097	High Similarity	NPC110776
0.9097	High Similarity	NPC131568
0.9097	High Similarity	NPC271590
0.9097	High Similarity	NPC131579
0.9085	High Similarity	NPC477272
0.9078	High Similarity	NPC470672
0.9078	High Similarity	NPC470671
0.9078	High Similarity	NPC474487
0.9078	High Similarity	NPC474504
0.9048	High Similarity	NPC29777
0.9048	High Similarity	NPC471115
0.9041	High Similarity	NPC145467
0.9041	High Similarity	NPC39195
0.9034	High Similarity	NPC285630
0.9034	High Similarity	NPC127059
0.9028	High Similarity	NPC125894
0.9028	High Similarity	NPC278249
0.9028	High Similarity	NPC316816
0.9028	High Similarity	NPC77794
0.9028	High Similarity	NPC107177
0.9028	High Similarity	NPC478086
0.9028	High Similarity	NPC18886
0.9028	High Similarity	NPC166138
0.9028	High Similarity	NPC18585
0.9028	High Similarity	NPC81697
0.9028	High Similarity	NPC106985
0.9028	High Similarity	NPC223812
0.9028	High Similarity	NPC214166
0.9028	High Similarity	NPC85162
0.9021	High Similarity	NPC248372
0.9021	High Similarity	NPC110038
0.9014	High Similarity	NPC23257
0.9014	High Similarity	NPC240305
0.898	High Similarity	NPC471114
0.8973	High Similarity	NPC300988
0.8973	High Similarity	NPC296998
0.8973	High Similarity	NPC473077
0.8973	High Similarity	NPC10990
0.8966	High Similarity	NPC473014
0.8966	High Similarity	NPC473013
0.8966	High Similarity	NPC235217
0.8966	High Similarity	NPC311144
0.8966	High Similarity	NPC473015
0.8966	High Similarity	NPC209040
0.8958	High Similarity	NPC223500
0.8958	High Similarity	NPC220998
0.8958	High Similarity	NPC66515
0.8958	High Similarity	NPC228504
0.8958	High Similarity	NPC265040
0.8958	High Similarity	NPC1089
0.8958	High Similarity	NPC202981
0.8958	High Similarity	NPC328164
0.8958	High Similarity	NPC32739
0.8958	High Similarity	NPC182852
0.8958	High Similarity	NPC166934
0.8958	High Similarity	NPC40833
0.8958	High Similarity	NPC276565
0.8958	High Similarity	NPC148757
0.8958	High Similarity	NPC37496
0.8958	High Similarity	NPC296917
0.8958	High Similarity	NPC144499
0.8958	High Similarity	NPC76372
0.8958	High Similarity	NPC324134
0.8958	High Similarity	NPC306829
0.8958	High Similarity	NPC161506
0.8958	High Similarity	NPC76338
0.8958	High Similarity	NPC10937
0.8958	High Similarity	NPC324436
0.8958	High Similarity	NPC125855
0.8958	High Similarity	NPC78
0.8958	High Similarity	NPC166482
0.8958	High Similarity	NPC107572
0.8958	High Similarity	NPC167624
0.8958	High Similarity	NPC194432
0.8958	High Similarity	NPC64915
0.8958	High Similarity	NPC227579
0.8958	High Similarity	NPC177354
0.8951	High Similarity	NPC129853
0.8951	High Similarity	NPC471587
0.8951	High Similarity	NPC284550
0.8951	High Similarity	NPC76445
0.8944	High Similarity	NPC54820
0.8944	High Similarity	NPC248995
0.8944	High Similarity	NPC131130
0.8944	High Similarity	NPC470669
0.8944	High Similarity	NPC268178
0.8944	High Similarity	NPC180501
0.8944	High Similarity	NPC272844
0.8944	High Similarity	NPC470668
0.8944	High Similarity	NPC254168
0.8936	High Similarity	NPC187826
0.8936	High Similarity	NPC156910
0.8921	High Similarity	NPC103105
0.8921	High Similarity	NPC285054
0.8904	High Similarity	NPC472629
0.8904	High Similarity	NPC267375
0.8904	High Similarity	NPC83357
0.8904	High Similarity	NPC73320
0.8904	High Similarity	NPC20488
0.8904	High Similarity	NPC299011
0.8904	High Similarity	NPC142405
0.8904	High Similarity	NPC111786
0.8904	High Similarity	NPC475052
0.8904	High Similarity	NPC214774
0.8904	High Similarity	NPC301276
0.8904	High Similarity	NPC176229
0.8904	High Similarity	NPC312973
0.8904	High Similarity	NPC54577
0.8904	High Similarity	NPC246948
0.8904	High Similarity	NPC88964
0.8904	High Similarity	NPC195621
0.8904	High Similarity	NPC470647
0.8904	High Similarity	NPC67805
0.8897	High Similarity	NPC150408
0.8897	High Similarity	NPC113770
0.8897	High Similarity	NPC91560
0.8897	High Similarity	NPC39329
0.8897	High Similarity	NPC310130
0.8897	High Similarity	NPC221432
0.8897	High Similarity	NPC143896
0.8897	High Similarity	NPC175504
0.8897	High Similarity	NPC257097
0.8897	High Similarity	NPC185276
0.8897	High Similarity	NPC164980
0.8897	High Similarity	NPC75049
0.8897	High Similarity	NPC219915
0.8897	High Similarity	NPC169591
0.8897	High Similarity	NPC68104
0.8897	High Similarity	NPC149026
0.8889	High Similarity	NPC282300
0.8889	High Similarity	NPC3188
0.8889	High Similarity	NPC312391
0.8889	High Similarity	NPC316911
0.8889	High Similarity	NPC17170
0.8889	High Similarity	NPC166689
0.8889	High Similarity	NPC96408
0.8889	High Similarity	NPC279650
0.8889	High Similarity	NPC4743
0.8889	High Similarity	NPC316560
0.8889	High Similarity	NPC213322
0.8889	High Similarity	NPC156190
0.8889	High Similarity	NPC470555
0.8889	High Similarity	NPC258630
0.8889	High Similarity	NPC324386
0.8881	High Similarity	NPC472343
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC316480
0.8881	High Similarity	NPC53181
0.8867	High Similarity	NPC472799
0.8859	High Similarity	NPC209142
0.8859	High Similarity	NPC178484
0.8859	High Similarity	NPC312549
0.8859	High Similarity	NPC476162
0.8851	High Similarity	NPC164205
0.8851	High Similarity	NPC104236
0.8844	High Similarity	NPC79469
0.8844	High Similarity	NPC470670
0.8844	High Similarity	NPC472627
0.8844	High Similarity	NPC110303
0.8844	High Similarity	NPC201731
0.8844	High Similarity	NPC473133
0.8844	High Similarity	NPC283234
0.8844	High Similarity	NPC97716
0.8844	High Similarity	NPC23728
0.8844	High Similarity	NPC285748
0.8844	High Similarity	NPC104406
0.8844	High Similarity	NPC47388
0.8844	High Similarity	NPC24673
0.8844	High Similarity	NPC237635
0.8836	High Similarity	NPC236766
0.8836	High Similarity	NPC124780
0.8836	High Similarity	NPC470890
0.8836	High Similarity	NPC470673
0.8836	High Similarity	NPC470674
0.8836	High Similarity	NPC197252
0.8836	High Similarity	NPC206212
0.8836	High Similarity	NPC311741
0.8836	High Similarity	NPC71184
0.8836	High Similarity	NPC234629
0.8836	High Similarity	NPC87486
0.8836	High Similarity	NPC184649
0.8836	High Similarity	NPC117716

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 NPC5990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	985
0.2-0.3	1723
0.3-0.4	2654
0.4-0.5	1909
0.5-0.6	1077
0.6-0.7	339
0.7-0.8	106
0.8-0.85	18
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8808	High Similarity	NPD8443	Clinical (unspecified phase)
0.8707	High Similarity	NPD4378	Clinical (unspecified phase)
0.8621	High Similarity	NPD2800	Approved
0.8611	High Similarity	NPD1552	Clinical (unspecified phase)
0.8611	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD7410	Clinical (unspecified phase)
0.8552	High Similarity	NPD1549	Phase 2
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD7411	Suspended
0.8462	Intermediate Similarity	NPD6651	Approved
0.8377	Intermediate Similarity	NPD7819	Suspended
0.8345	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8301	Intermediate Similarity	NPD4380	Phase 2
0.8288	Intermediate Similarity	NPD2796	Approved
0.8258	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1240	Approved
0.8194	Intermediate Similarity	NPD1934	Approved
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7768	Phase 2
0.8082	Intermediate Similarity	NPD1607	Approved
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.8041	Intermediate Similarity	NPD1551	Phase 2
0.8014	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6801	Discontinued
0.7947	Intermediate Similarity	NPD3750	Approved
0.7947	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2801	Approved
0.7908	Intermediate Similarity	NPD6799	Approved
0.7908	Intermediate Similarity	NPD1511	Approved
0.7888	Intermediate Similarity	NPD5494	Approved
0.7879	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3749	Approved
0.7871	Intermediate Similarity	NPD920	Approved
0.7843	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6599	Discontinued
0.7812	Intermediate Similarity	NPD3882	Suspended
0.7808	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1512	Approved
0.7805	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6166	Phase 2
0.7805	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6100	Approved
0.78	Intermediate Similarity	NPD6099	Approved
0.7798	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD5711	Approved
0.7791	Intermediate Similarity	NPD5710	Approved
0.7742	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.7683	Intermediate Similarity	NPD6232	Discontinued
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7651	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7616	Intermediate Similarity	NPD3748	Approved
0.7597	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.7569	Intermediate Similarity	NPD4749	Approved
0.7568	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7054	Approved
0.756	Intermediate Similarity	NPD5844	Phase 1
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD1247	Approved
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7458	Intermediate Similarity	NPD4360	Phase 2
0.7458	Intermediate Similarity	NPD4363	Phase 3
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.745	Intermediate Similarity	NPD2313	Discontinued
0.745	Intermediate Similarity	NPD3268	Approved
0.7438	Intermediate Similarity	NPD3226	Approved
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7421	Intermediate Similarity	NPD5403	Approved
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD9717	Approved
0.7347	Intermediate Similarity	NPD2797	Approved
0.7347	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2309	Approved
0.7318	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4361	Phase 2
0.7315	Intermediate Similarity	NPD6832	Phase 2
0.731	Intermediate Similarity	NPD422	Phase 1
0.731	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2798	Approved
0.7296	Intermediate Similarity	NPD5401	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2403	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7256	Intermediate Similarity	NPD5761	Phase 2
0.7256	Intermediate Similarity	NPD5760	Phase 2
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7212	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD2654	Approved
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7179	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7124	Intermediate Similarity	NPD943	Approved
0.7118	Intermediate Similarity	NPD3926	Phase 2
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7114	Intermediate Similarity	NPD3267	Approved
0.7114	Intermediate Similarity	NPD3266	Approved
0.711	Intermediate Similarity	NPD1729	Discontinued
0.7108	Intermediate Similarity	NPD4288	Approved
0.7083	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD230	Phase 1
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3225	Approved
0.7044	Intermediate Similarity	NPD7003	Approved
0.7042	Intermediate Similarity	NPD1241	Discontinued
0.7039	Intermediate Similarity	NPD4287	Approved
0.703	Intermediate Similarity	NPD5890	Approved
0.703	Intermediate Similarity	NPD5889	Approved
0.7029	Intermediate Similarity	NPD6104	Discontinued
0.7025	Intermediate Similarity	NPD2424	Discontinued
0.702	Intermediate Similarity	NPD2861	Phase 2
0.7014	Intermediate Similarity	NPD9493	Approved
0.7013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1613	Approved
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD7199	Phase 2
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3751	Discontinued
0.6993	Remote Similarity	NPD1296	Phase 2
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD411	Approved
0.6993	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6585	Discontinued
0.6968	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD1933	Approved
0.6968	Remote Similarity	NPD447	Suspended
0.6954	Remote Similarity	NPD1019	Discontinued
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8313	Approved
0.6949	Remote Similarity	NPD8312	Approved
0.6939	Remote Similarity	NPD17	Approved
0.6936	Remote Similarity	NPD3446	Phase 1
0.6933	Remote Similarity	NPD8651	Approved
0.6931	Remote Similarity	NPD7584	Approved
0.6919	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3972	Approved
0.6908	Remote Similarity	NPD9494	Approved
0.6908	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4307	Phase 2
0.6903	Remote Similarity	NPD4060	Phase 1
0.6899	Remote Similarity	NPD4476	Approved
0.6899	Remote Similarity	NPD4477	Approved
0.6897	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1164	Approved
0.6886	Remote Similarity	NPD7577	Discontinued
0.6883	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3787	Discontinued
0.6855	Remote Similarity	NPD1471	Phase 3
0.6846	Remote Similarity	NPD1201	Approved
0.6845	Remote Similarity	NPD8455	Phase 2
0.6835	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8150	Discontinued
0.6829	Remote Similarity	NPD6273	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