NPASS Compound

Structure

NPC5253 OpenBabel07101719252D 32 36 0 0 1 0 0 0 0 0999 V2000 3.2194 -1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2447 -1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0854 2.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9514 1.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9514 3.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8175 1.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 1.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 -1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 -1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0854 1.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8175 2.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 1.1413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4873 1.1413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2618 1.3143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4873 0.1413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -1.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 1.9356 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1857 1.9356 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3534 -0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 -0.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1730 1.3143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1857 0.6930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7618 2.1803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6835 3.1413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 -2.8587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 2.8017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3143 2.8017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2194 0.1413 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 -0.9031 0.6930 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 24 1 0 0 0 0 9 17 2 0 0 0 0 9 20 1 0 0 0 0 10 17 1 0 0 0 0 10 21 2 0 0 0 0 12 25 1 0 0 0 0 13 11 1 1 0 0 0 13 29 1 0 0 0 0 14 7 1 6 0 0 0 14 16 1 0 0 0 0 14 30 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 31 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 6 0 0 0 20 29 1 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 31 1 6 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.16
Volume:	426.875
LogP:	1.921
LogD:	1.537
LogS:	-3.522
# Rotatable Bonds:	2
TPSA:	138.07
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	4.606
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.92
MDCK Permeability:	1.2991288713237736e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	95.63764190673828%
Volume Distribution (VD):	0.717
Pgp-substrate:	5.599090099334717%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.632
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	6.343
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.934
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.576
Respiratory Toxicity:	0.636

Download Data

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

Natural Product: NPC5253

Natural Product ID:	NPC5253
*Common Name:**	Abacopterin F
IUPAC Name:	n.a.
Synonyms:	Abacopterin F
Standard InCHIKey:	IAQOOCVBIITHOV-UWKTVYOHSA-N
Standard InCHI:	InChI=1S/C23H26O9/c1-9-17(26)10(2)21-16-14(7-13(29-20(9)16)11-3-5-12(25)6-4-11)30-22-19(28)18(27)15(8-24)31-23(22)32-21/h3-6,13-15,18-19,22-28H,7-8H2,1-2H3/t13-,14+,15+,18+,19-,22+,23-/m0/s1
SMILES:	Cc1c(c(C)c2c3[C@@H](C[C@@H](c4ccc(cc4)O)Oc13)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1O2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403121
PubChem CID:	23657297
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002993] 7-hydroxyflavonoids

*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
NPO16914	Abacopteris penangiana	n.a.	n.a.	n.a.	n.a.	rhizome	n.a.	PMID[16499328]
NPO16914	Abacopteris penangiana	n.a.	n.a.	n.a.	Rhizomes	n.a.	n.a.	PMID[16499328]
NPO16914	Abacopteris penangiana	n.a.	n.a.	n.a.	aerial parts	Jiangxi Province, China	2004-JUN	PMID[17922550]
NPO16914	Abacopteris penangiana	n.a.	n.a.	n.a.	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.32	mM	PMID[487812]

☑ 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 NPC5253 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	403
0.1-0.2	1507
0.2-0.3	4062
0.3-0.4	10549
0.4-0.5	8031
0.5-0.6	4785
0.6-0.7	7319
0.7-0.8	5087
0.8-0.85	739
0.85-0.9	181
0.9-0.95	23
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230718
1.0	High Similarity	NPC139976
1.0	High Similarity	NPC128337
1.0	High Similarity	NPC84207
1.0	High Similarity	NPC49542
0.971	High Similarity	NPC74320
0.971	High Similarity	NPC107120
0.9708	High Similarity	NPC177597
0.9701	High Similarity	NPC87777
0.9701	High Similarity	NPC262328
0.9565	High Similarity	NPC225445
0.9493	High Similarity	NPC116922
0.9281	High Similarity	NPC472353
0.9209	High Similarity	NPC108674
0.9209	High Similarity	NPC210192
0.9155	High Similarity	NPC125755
0.9149	High Similarity	NPC469313
0.9149	High Similarity	NPC76176
0.9149	High Similarity	NPC138227
0.9149	High Similarity	NPC168579
0.9124	High Similarity	NPC79957
0.9124	High Similarity	NPC238243
0.9111	High Similarity	NPC103799
0.9091	High Similarity	NPC15538
0.9091	High Similarity	NPC473480
0.9085	High Similarity	NPC277867
0.9085	High Similarity	NPC161700
0.9085	High Similarity	NPC226722
0.9078	High Similarity	NPC37793
0.9058	High Similarity	NPC138350
0.9058	High Similarity	NPC197723
0.9058	High Similarity	NPC40664
0.9058	High Similarity	NPC165482
0.9058	High Similarity	NPC3293
0.9051	High Similarity	NPC130496
0.9051	High Similarity	NPC188555
0.9021	High Similarity	NPC248053
0.9021	High Similarity	NPC155564
0.9021	High Similarity	NPC102280
0.8993	High Similarity	NPC134260
0.8978	High Similarity	NPC115022
0.8978	High Similarity	NPC215037
0.8978	High Similarity	NPC294166
0.8973	High Similarity	NPC259707
0.8951	High Similarity	NPC475096
0.8936	High Similarity	NPC5155
0.8929	High Similarity	NPC475836
0.8905	High Similarity	NPC85799
0.8905	High Similarity	NPC26080
0.8905	High Similarity	NPC303422
0.8905	High Similarity	NPC165686
0.8897	High Similarity	NPC280945
0.8889	High Similarity	NPC190714
0.8889	High Similarity	NPC87224
0.8889	High Similarity	NPC274717
0.8889	High Similarity	NPC222572
0.8889	High Similarity	NPC99515
0.8881	High Similarity	NPC276212
0.8873	High Similarity	NPC475084
0.8873	High Similarity	NPC189115
0.8844	High Similarity	NPC473621
0.8841	High Similarity	NPC92805
0.8832	High Similarity	NPC121376
0.8832	High Similarity	NPC475067
0.8828	High Similarity	NPC87950
0.8828	High Similarity	NPC471764
0.8828	High Similarity	NPC227902
0.8811	High Similarity	NPC473044
0.8806	High Similarity	NPC167571
0.8806	High Similarity	NPC278552
0.8806	High Similarity	NPC207179
0.8806	High Similarity	NPC285040
0.8806	High Similarity	NPC102540
0.8806	High Similarity	NPC103420
0.8806	High Similarity	NPC188022
0.8806	High Similarity	NPC17809
0.8803	High Similarity	NPC273932
0.8803	High Similarity	NPC257095
0.8803	High Similarity	NPC469661
0.8803	High Similarity	NPC89686
0.8803	High Similarity	NPC100482
0.8803	High Similarity	NPC277331
0.8786	High Similarity	NPC262585
0.8786	High Similarity	NPC20829
0.8786	High Similarity	NPC18189
0.8784	High Similarity	NPC59692
0.8784	High Similarity	NPC21902
0.8777	High Similarity	NPC124085
0.8777	High Similarity	NPC117048
0.8776	High Similarity	NPC472710
0.8776	High Similarity	NPC472709
0.8767	High Similarity	NPC270751
0.8767	High Similarity	NPC175976
0.875	High Similarity	NPC25292
0.875	High Similarity	NPC473045
0.8741	High Similarity	NPC469559
0.8731	High Similarity	NPC246648
0.8731	High Similarity	NPC106914
0.8731	High Similarity	NPC134195
0.8731	High Similarity	NPC197351
0.8731	High Similarity	NPC86502
0.8723	High Similarity	NPC124149
0.8716	High Similarity	NPC471403
0.8705	High Similarity	NPC85435
0.869	High Similarity	NPC85624
0.8686	High Similarity	NPC218003
0.8681	High Similarity	NPC252169
0.8676	High Similarity	NPC149796
0.8662	High Similarity	NPC212770
0.8662	High Similarity	NPC98777
0.8658	High Similarity	NPC53587
0.8658	High Similarity	NPC44192
0.8658	High Similarity	NPC322899
0.8658	High Similarity	NPC226108
0.8658	High Similarity	NPC272552
0.8658	High Similarity	NPC176186
0.8658	High Similarity	NPC469944
0.8658	High Similarity	NPC46283
0.8658	High Similarity	NPC134911
0.8658	High Similarity	NPC169404
0.8657	High Similarity	NPC76465
0.8657	High Similarity	NPC38761
0.8652	High Similarity	NPC166180
0.8652	High Similarity	NPC242028
0.8652	High Similarity	NPC3049
0.8652	High Similarity	NPC470802
0.8652	High Similarity	NPC203230
0.8649	High Similarity	NPC107197
0.8639	High Similarity	NPC169510
0.8623	High Similarity	NPC262606
0.8623	High Similarity	NPC474491
0.8621	High Similarity	NPC475492
0.8613	High Similarity	NPC53986
0.8613	High Similarity	NPC38664
0.8601	High Similarity	NPC106944
0.86	High Similarity	NPC306267
0.86	High Similarity	NPC78809
0.86	High Similarity	NPC150442
0.86	High Similarity	NPC20050
0.8592	High Similarity	NPC65530
0.8592	High Similarity	NPC59324
0.8592	High Similarity	NPC211549
0.8592	High Similarity	NPC474687
0.8582	High Similarity	NPC61946
0.8582	High Similarity	NPC36016
0.8582	High Similarity	NPC100099
0.8582	High Similarity	NPC473413
0.8582	High Similarity	NPC476142
0.8582	High Similarity	NPC137580
0.8571	High Similarity	NPC275284
0.8571	High Similarity	NPC213074
0.8571	High Similarity	NPC31325
0.8571	High Similarity	NPC15956
0.8571	High Similarity	NPC224674
0.8571	High Similarity	NPC193473
0.8571	High Similarity	NPC39657
0.8571	High Similarity	NPC114505
0.8571	High Similarity	NPC296377
0.8562	High Similarity	NPC185231
0.8562	High Similarity	NPC43508
0.8562	High Similarity	NPC476301
0.8561	High Similarity	NPC293203
0.8561	High Similarity	NPC118683
0.8561	High Similarity	NPC12875
0.8561	High Similarity	NPC17343
0.8561	High Similarity	NPC280653
0.8561	High Similarity	NPC207892
0.8561	High Similarity	NPC164804
0.8561	High Similarity	NPC300875
0.8561	High Similarity	NPC164574
0.8561	High Similarity	NPC150011
0.8561	High Similarity	NPC211413
0.8561	High Similarity	NPC118114
0.8561	High Similarity	NPC129106
0.8561	High Similarity	NPC228369
0.8561	High Similarity	NPC196765
0.8561	High Similarity	NPC244888
0.8561	High Similarity	NPC268917
0.8561	High Similarity	NPC206224
0.8561	High Similarity	NPC236014
0.8561	High Similarity	NPC68205
0.8561	High Similarity	NPC129784
0.8561	High Similarity	NPC162801
0.8561	High Similarity	NPC476166
0.8553	High Similarity	NPC206378
0.8552	High Similarity	NPC81638
0.8551	High Similarity	NPC93962
0.8551	High Similarity	NPC134360
0.8533	High Similarity	NPC302610
0.8533	High Similarity	NPC233467
0.8531	High Similarity	NPC292487
0.8523	High Similarity	NPC145979
0.8523	High Similarity	NPC469706
0.8523	High Similarity	NPC469707
0.8523	High Similarity	NPC182368
0.8523	High Similarity	NPC225815
0.8523	High Similarity	NPC185955
0.8523	High Similarity	NPC260781
0.8523	High Similarity	NPC9933
0.8523	High Similarity	NPC214326

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 NPC5253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	849
0.2-0.3	1773
0.3-0.4	2801
0.4-0.5	1744
0.5-0.6	970
0.6-0.7	578
0.7-0.8	97
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8507	High Similarity	NPD1091	Approved
0.8489	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1613	Approved
0.8369	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD4908	Phase 1
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1610	Phase 2
0.8085	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1548	Phase 1
0.8065	Intermediate Similarity	NPD8455	Phase 2
0.8028	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7974	Intermediate Similarity	NPD1653	Approved
0.7931	Intermediate Similarity	NPD5124	Phase 1
0.7931	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6674	Discontinued
0.7914	Intermediate Similarity	NPD7054	Approved
0.7881	Intermediate Similarity	NPD5058	Phase 3
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7871	Intermediate Similarity	NPD4380	Phase 2
0.7866	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD4625	Phase 3
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7744	Intermediate Similarity	NPD7228	Approved
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7703	Intermediate Similarity	NPD4538	Approved
0.7703	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4536	Approved
0.7688	Intermediate Similarity	NPD7075	Discontinued
0.7682	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1652	Phase 2
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7213	Phase 3
0.7597	Intermediate Similarity	NPD7212	Phase 2
0.7584	Intermediate Similarity	NPD7097	Phase 1
0.7552	Intermediate Similarity	NPD8651	Approved
0.7547	Intermediate Similarity	NPD37	Approved
0.7547	Intermediate Similarity	NPD6801	Discontinued
0.7533	Intermediate Similarity	NPD5960	Phase 3
0.7533	Intermediate Similarity	NPD5588	Approved
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7843	Approved
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7465	Intermediate Similarity	NPD422	Phase 1
0.7463	Intermediate Similarity	NPD2684	Approved
0.7453	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7199	Phase 2
0.7438	Intermediate Similarity	NPD1934	Approved
0.7436	Intermediate Similarity	NPD7447	Phase 1
0.7436	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD290	Approved
0.7386	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7353	Intermediate Similarity	NPD7240	Approved
0.7342	Intermediate Similarity	NPD5403	Approved
0.7338	Intermediate Similarity	NPD7157	Approved
0.7325	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5126	Approved
0.7324	Intermediate Similarity	NPD5125	Phase 3
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD8313	Approved
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6959	Discontinued
0.7215	Intermediate Similarity	NPD5401	Approved
0.7203	Intermediate Similarity	NPD6516	Phase 2
0.7203	Intermediate Similarity	NPD5846	Approved
0.72	Intermediate Similarity	NPD6233	Phase 2
0.7195	Intermediate Similarity	NPD7768	Phase 2
0.719	Intermediate Similarity	NPD7033	Discontinued
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7179	Intermediate Similarity	NPD4535	Phase 3
0.7179	Intermediate Similarity	NPD3750	Approved
0.7178	Intermediate Similarity	NPD7819	Suspended
0.7162	Intermediate Similarity	NPD3018	Phase 2
0.7152	Intermediate Similarity	NPD6799	Approved
0.7134	Intermediate Similarity	NPD5402	Approved
0.7123	Intermediate Similarity	NPD3685	Discontinued
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6671	Approved
0.7079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4108	Discontinued
0.7073	Intermediate Similarity	NPD2801	Approved
0.707	Intermediate Similarity	NPD4628	Phase 3
0.7066	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7048	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7584	Approved
0.7032	Intermediate Similarity	NPD2796	Approved
0.703	Intermediate Similarity	NPD3817	Phase 2
0.7018	Intermediate Similarity	NPD3751	Discontinued
0.7015	Intermediate Similarity	NPD940	Approved
0.7015	Intermediate Similarity	NPD846	Approved
0.7007	Intermediate Similarity	NPD2982	Phase 2
0.7007	Intermediate Similarity	NPD2983	Phase 2
0.7007	Intermediate Similarity	NPD6583	Phase 3
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6582	Phase 2
0.7005	Intermediate Similarity	NPD7585	Approved
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5535	Approved
0.6994	Remote Similarity	NPD6599	Discontinued
0.6993	Remote Similarity	NPD4340	Discontinued
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.6986	Remote Similarity	NPD3705	Approved
0.697	Remote Similarity	NPD1465	Phase 2
0.6968	Remote Similarity	NPD1510	Phase 2
0.6962	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7466	Approved
0.6962	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3225	Approved
0.6952	Remote Similarity	NPD7583	Approved
0.6951	Remote Similarity	NPD6072	Discontinued
0.694	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2981	Phase 2
0.6937	Remote Similarity	NPD1511	Approved
0.6933	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1240	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6913	Remote Similarity	NPD2797	Approved
0.691	Remote Similarity	NPD6843	Phase 3
0.691	Remote Similarity	NPD6841	Approved
0.691	Remote Similarity	NPD6842	Approved
0.6909	Remote Similarity	NPD4433	Discontinued
0.6899	Remote Similarity	NPD5061	Approved
0.6899	Remote Similarity	NPD5062	Approved
0.6897	Remote Similarity	NPD1357	Approved
0.6893	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3882	Suspended
0.6883	Remote Similarity	NPD5735	Approved
0.6882	Remote Similarity	NPD7680	Approved
0.6882	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD6004	Phase 3
0.6879	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6002	Phase 3
0.6879	Remote Similarity	NPD6005	Phase 3
0.6879	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6667	Approved
0.6875	Remote Similarity	NPD6666	Approved
0.6867	Remote Similarity	NPD6584	Phase 3
0.6867	Remote Similarity	NPD3690	Phase 2
0.6867	Remote Similarity	NPD3691	Phase 2
0.6863	Remote Similarity	NPD4062	Phase 3
0.6859	Remote Similarity	NPD3748	Approved
0.6855	Remote Similarity	NPD3892	Phase 2
0.6852	Remote Similarity	NPD1512	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6839	Remote Similarity	NPD1607	Approved
0.6832	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4477	Approved
0.6815	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD4476	Approved
0.6815	Remote Similarity	NPD2935	Discontinued
0.6813	Remote Similarity	NPD2677	Approved
0.6811	Remote Similarity	NPD6782	Approved
0.6811	Remote Similarity	NPD6779	Approved
0.6811	Remote Similarity	NPD6781	Approved
0.6811	Remote Similarity	NPD6777	Approved
0.6811	Remote Similarity	NPD6776	Approved
0.6811	Remote Similarity	NPD6778	Approved
0.6811	Remote Similarity	NPD6780	Approved
0.681	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7783	Phase 2
0.6803	Remote Similarity	NPD3496	Discontinued
0.6797	Remote Similarity	NPD3268	Approved
0.6795	Remote Similarity	NPD2200	Suspended
0.679	Remote Similarity	NPD3536	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data