NPASS Compound

Structure

NPC471824 OpenBabel07101718312D 42 44 0 0 1 0 0 0 0 0999 V2000 12.1244 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 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 7.7942 -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 10.3923 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 6.0622 -3.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 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 11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 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 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 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 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 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 8.6603 -2.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 37 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 8 40 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 19 23 1 0 0 0 0 19 30 2 0 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 26 2 0 0 0 0 21 31 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 33 1 0 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 26 41 1 0 0 0 0 27 15 1 1 0 0 0 27 32 1 0 0 0 0 27 42 1 0 0 0 0 28 34 2 0 0 0 0 28 41 1 0 0 0 0 29 35 2 0 0 0 0 29 42 1 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.25
Volume:	595.26
LogP:	5.852
LogD:	3.479
LogS:	-3.827
# Rotatable Bonds:	13
TPSA:	133.89
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	3.866
Fsp3:	0.375
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.739
MDCK Permeability:	1.9154609617544338e-05
Pgp-inhibitor:	0.746
Pgp-substrate:	0.131
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	78.19973754882812%
Volume Distribution (VD):	0.486
Pgp-substrate:	30.96795654296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.676
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.505
CYP2D6-substrate:	0.728
CYP3A4-inhibitor:	0.845
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	9.413
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.886
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.48

Download Data

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

Natural Product: NPC471824

Natural Product ID:	NPC471824
*Common Name:**	Toddalin B
IUPAC Name:	[(2S)-1-(5,7-dimethoxy-2-oxochromen-6-yl)-3-hydroxy-3-methylbutan-2-yl] (E)-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoate
Synonyms:
Standard InCHIKey:	KDIPEMZSOZWDHL-OTQLOIIPSA-N
Standard InCHI:	InChI=1S/C32H38O10/c1-18(2)9-10-20-24(37-5)16-23(33)19(30(20)39-7)11-13-29(35)42-27(32(3,4)36)15-22-25(38-6)17-26-21(31(22)40-8)12-14-28(34)41-26/h9,11-14,16-17,27,33,36H,10,15H2,1-8H3/b13-11+/t27-/m0/s1
SMILES:	COc1cc2oc(=O)ccc2c(c1C[C@@H](C(O)(C)C)OC(=O)/C=C/c1c(O)cc(c(c1OC)CC=C(C)C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235991
PubChem CID:	90655367
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0002503] Hydroxycinnamic acids

*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
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7213	Toddalia asiatica	Species	Rutaceae	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
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	7810.0	nM	PMID[545090]

☑ 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 NPC471824 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	375
0.1-0.2	1497
0.2-0.3	3476
0.3-0.4	8137
0.4-0.5	10302
0.5-0.6	4173
0.6-0.7	5492
0.7-0.8	4589
0.8-0.85	3013
0.85-0.9	1402
0.9-0.95	229
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9353	High Similarity	NPC152771
0.9353	High Similarity	NPC195357
0.9348	High Similarity	NPC151946
0.9348	High Similarity	NPC279573
0.9343	High Similarity	NPC38099
0.9343	High Similarity	NPC26954
0.9281	High Similarity	NPC312881
0.9275	High Similarity	NPC184861
0.9275	High Similarity	NPC225106
0.9275	High Similarity	NPC281014
0.9275	High Similarity	NPC232246
0.9275	High Similarity	NPC294456
0.9275	High Similarity	NPC212124
0.9275	High Similarity	NPC153818
0.9275	High Similarity	NPC155963
0.927	High Similarity	NPC472525
0.9225	High Similarity	NPC469701
0.9214	High Similarity	NPC287286
0.9209	High Similarity	NPC211110
0.9203	High Similarity	NPC78746
0.9203	High Similarity	NPC188380
0.9203	High Similarity	NPC224543
0.9197	High Similarity	NPC50896
0.9197	High Similarity	NPC180716
0.9197	High Similarity	NPC326600
0.9197	High Similarity	NPC204353
0.9197	High Similarity	NPC213173
0.9197	High Similarity	NPC62366
0.9197	High Similarity	NPC224475
0.913	High Similarity	NPC33986
0.9124	High Similarity	NPC207002
0.9124	High Similarity	NPC133956
0.9124	High Similarity	NPC296624
0.9124	High Similarity	NPC318400
0.9124	High Similarity	NPC471910
0.9124	High Similarity	NPC167111
0.9124	High Similarity	NPC31849
0.9091	High Similarity	NPC85624
0.9058	High Similarity	NPC267412
0.9058	High Similarity	NPC127888
0.9058	High Similarity	NPC287182
0.9058	High Similarity	NPC84894
0.9058	High Similarity	NPC166672
0.9058	High Similarity	NPC98179
0.9058	High Similarity	NPC195343
0.9058	High Similarity	NPC253574
0.9058	High Similarity	NPC198381
0.9058	High Similarity	NPC18804
0.9058	High Similarity	NPC131950
0.9058	High Similarity	NPC74655
0.9058	High Similarity	NPC100986
0.9058	High Similarity	NPC260265
0.9058	High Similarity	NPC319859
0.9058	High Similarity	NPC47163
0.9058	High Similarity	NPC164269
0.9051	High Similarity	NPC194277
0.9044	High Similarity	NPC32463
0.9041	High Similarity	NPC103116
0.9034	High Similarity	NPC169510
0.8993	High Similarity	NPC86892
0.8993	High Similarity	NPC281241
0.8993	High Similarity	NPC471909
0.8993	High Similarity	NPC472424
0.8993	High Similarity	NPC471625
0.8986	High Similarity	NPC469449
0.8986	High Similarity	NPC163557
0.8978	High Similarity	NPC272650
0.8978	High Similarity	NPC29734
0.8978	High Similarity	NPC267336
0.8966	High Similarity	NPC87950
0.8966	High Similarity	NPC471764
0.8966	High Similarity	NPC296377
0.8958	High Similarity	NPC226722
0.8936	High Similarity	NPC471071
0.8936	High Similarity	NPC471072
0.8936	High Similarity	NPC471070
0.8929	High Similarity	NPC476455
0.8929	High Similarity	NPC128529
0.8929	High Similarity	NPC283019
0.8929	High Similarity	NPC471630
0.8929	High Similarity	NPC160727
0.8929	High Similarity	NPC55615
0.8929	High Similarity	NPC177281
0.8929	High Similarity	NPC149320
0.8921	High Similarity	NPC307412
0.8921	High Similarity	NPC55149
0.8913	High Similarity	NPC14248
0.8905	High Similarity	NPC113098
0.8904	High Similarity	NPC476348
0.8904	High Similarity	NPC187398
0.8897	High Similarity	NPC185066
0.8889	High Similarity	NPC471763
0.8865	High Similarity	NPC471069
0.8865	High Similarity	NPC471068
0.8857	High Similarity	NPC469675
0.8849	High Similarity	NPC7526
0.8849	High Similarity	NPC222036
0.8849	High Similarity	NPC92805
0.8844	High Similarity	NPC30688
0.8844	High Similarity	NPC176903
0.8841	High Similarity	NPC103799
0.8836	High Similarity	NPC476347
0.8832	High Similarity	NPC168710
0.8828	High Similarity	NPC475719
0.8828	High Similarity	NPC101255
0.8828	High Similarity	NPC43716
0.8828	High Similarity	NPC295696
0.8824	High Similarity	NPC243688
0.8811	High Similarity	NPC183642
0.8811	High Similarity	NPC310370
0.8803	High Similarity	NPC35501
0.8803	High Similarity	NPC47040
0.8803	High Similarity	NPC278600
0.8803	High Similarity	NPC144512
0.8803	High Similarity	NPC137262
0.8803	High Similarity	NPC37428
0.8794	High Similarity	NPC18189
0.8794	High Similarity	NPC262585
0.8794	High Similarity	NPC20829
0.8786	High Similarity	NPC117048
0.8786	High Similarity	NPC124085
0.8784	High Similarity	NPC21184
0.8784	High Similarity	NPC205727
0.8784	High Similarity	NPC120426
0.8784	High Similarity	NPC294522
0.8768	High Similarity	NPC80170
0.8767	High Similarity	NPC40222
0.8767	High Similarity	NPC268515
0.8759	High Similarity	NPC87224
0.8759	High Similarity	NPC222572
0.8759	High Similarity	NPC469453
0.875	High Similarity	NPC125495
0.8732	High Similarity	NPC474886
0.8718	High Similarity	NPC471823
0.8714	High Similarity	NPC85435
0.8707	High Similarity	NPC15577
0.8705	High Similarity	NPC250727
0.8699	High Similarity	NPC71739
0.8696	High Similarity	NPC134360
0.869	High Similarity	NPC110067
0.869	High Similarity	NPC91492
0.869	High Similarity	NPC256555
0.869	High Similarity	NPC34245
0.869	High Similarity	NPC7439
0.8686	High Similarity	NPC121740
0.8686	High Similarity	NPC224774
0.8686	High Similarity	NPC258567
0.8681	High Similarity	NPC170812
0.8676	High Similarity	NPC93219
0.8676	High Similarity	NPC244495
0.8676	High Similarity	NPC168259
0.8675	High Similarity	NPC268484
0.8675	High Similarity	NPC8712
0.8667	High Similarity	NPC176186
0.8667	High Similarity	NPC169404
0.8667	High Similarity	NPC163598
0.8667	High Similarity	NPC53587
0.8667	High Similarity	NPC120774
0.8667	High Similarity	NPC264875
0.8662	High Similarity	NPC283331
0.8662	High Similarity	NPC3049
0.8643	High Similarity	NPC19157
0.8643	High Similarity	NPC469956
0.8639	High Similarity	NPC107120
0.8639	High Similarity	NPC205361
0.8639	High Similarity	NPC74320
0.863	High Similarity	NPC476457
0.863	High Similarity	NPC36732
0.8623	High Similarity	NPC219923
0.8623	High Similarity	NPC199204
0.8623	High Similarity	NPC274717
0.8618	High Similarity	NPC279218
0.8618	High Similarity	NPC108937
0.8613	High Similarity	NPC471826
0.8611	High Similarity	NPC71903
0.8609	High Similarity	NPC150442
0.8609	High Similarity	NPC223720
0.8603	High Similarity	NPC201667
0.8603	High Similarity	NPC73413
0.8601	High Similarity	NPC474687
0.8601	High Similarity	NPC131198
0.8591	High Similarity	NPC475250
0.8582	High Similarity	NPC141822
0.8582	High Similarity	NPC469955
0.8582	High Similarity	NPC142563
0.8582	High Similarity	NPC1220
0.8582	High Similarity	NPC291551
0.8582	High Similarity	NPC241165
0.8582	High Similarity	NPC205797
0.8582	High Similarity	NPC469965
0.8582	High Similarity	NPC469952
0.8571	High Similarity	NPC66430
0.8571	High Similarity	NPC162801
0.8571	High Similarity	NPC106126
0.8571	High Similarity	NPC37009
0.8571	High Similarity	NPC244888
0.8571	High Similarity	NPC68205
0.8571	High Similarity	NPC108994
0.8571	High Similarity	NPC293203
0.8571	High Similarity	NPC118683

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 NPC471824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	901
0.2-0.3	1710
0.3-0.4	2558
0.4-0.5	1980
0.5-0.6	1085
0.6-0.7	381
0.7-0.8	137
0.8-0.85	55
0.85-0.9	13
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8582	High Similarity	NPD5124	Phase 1
0.8582	High Similarity	NPD5123	Clinical (unspecified phase)
0.8506	High Similarity	NPD7075	Discontinued
0.8382	Intermediate Similarity	NPD422	Phase 1
0.8312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1652	Phase 2
0.8247	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4380	Phase 2
0.8224	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD4908	Phase 1
0.8089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8088	Intermediate Similarity	NPD1548	Phase 1
0.8077	Intermediate Similarity	NPD7819	Suspended
0.8038	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD3750	Approved
0.7986	Intermediate Similarity	NPD1610	Phase 2
0.7972	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7411	Suspended
0.7922	Intermediate Similarity	NPD5403	Approved
0.7917	Intermediate Similarity	NPD3027	Phase 3
0.7911	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6799	Approved
0.7834	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5402	Approved
0.7799	Intermediate Similarity	NPD3817	Phase 2
0.7793	Intermediate Similarity	NPD4625	Phase 3
0.7792	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD1934	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD2797	Approved
0.7748	Intermediate Similarity	NPD1549	Phase 2
0.7744	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6798	Discontinued
0.7736	Intermediate Similarity	NPD8455	Phase 2
0.7733	Intermediate Similarity	NPD2796	Approved
0.7718	Intermediate Similarity	NPD7097	Phase 1
0.7703	Intermediate Similarity	NPD6355	Discontinued
0.7703	Intermediate Similarity	NPD4340	Discontinued
0.7692	Intermediate Similarity	NPD8651	Approved
0.7692	Intermediate Similarity	NPD3225	Approved
0.7682	Intermediate Similarity	NPD7266	Discontinued
0.7682	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD7033	Discontinued
0.7667	Intermediate Similarity	NPD1510	Phase 2
0.7658	Intermediate Similarity	NPD6599	Discontinued
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD2424	Discontinued
0.7625	Intermediate Similarity	NPD2801	Approved
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3268	Approved
0.7616	Intermediate Similarity	NPD2935	Discontinued
0.7616	Intermediate Similarity	NPD1551	Phase 2
0.7605	Intermediate Similarity	NPD7054	Approved
0.7568	Intermediate Similarity	NPD6233	Phase 2
0.756	Intermediate Similarity	NPD7472	Approved
0.756	Intermediate Similarity	NPD7074	Phase 3
0.7551	Intermediate Similarity	NPD7095	Approved
0.755	Intermediate Similarity	NPD4308	Phase 3
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.7534	Intermediate Similarity	NPD2861	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD7549	Discontinued
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7518	Intermediate Similarity	NPD7843	Approved
0.7518	Intermediate Similarity	NPD5535	Approved
0.7516	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7483	Intermediate Similarity	NPD1091	Approved
0.7483	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD920	Approved
0.7453	Intermediate Similarity	NPD37	Approved
0.7452	Intermediate Similarity	NPD7447	Phase 1
0.7451	Intermediate Similarity	NPD5762	Approved
0.7451	Intermediate Similarity	NPD5763	Approved
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7436	Intermediate Similarity	NPD6666	Approved
0.7436	Intermediate Similarity	NPD6667	Approved
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4965	Approved
0.7423	Intermediate Similarity	NPD4967	Phase 2
0.7423	Intermediate Similarity	NPD4966	Approved
0.7423	Intermediate Similarity	NPD3882	Suspended
0.7416	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3496	Discontinued
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.7405	Intermediate Similarity	NPD1512	Approved
0.74	Intermediate Similarity	NPD1240	Approved
0.7389	Intermediate Similarity	NPD7212	Phase 2
0.7389	Intermediate Similarity	NPD7213	Phase 3
0.7383	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7378	Intermediate Similarity	NPD3749	Approved
0.7372	Intermediate Similarity	NPD6190	Approved
0.7357	Intermediate Similarity	NPD7157	Approved
0.7355	Intermediate Similarity	NPD1243	Approved
0.7349	Intermediate Similarity	NPD6959	Discontinued
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7349	Intermediate Similarity	NPD8127	Discontinued
0.7343	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5960	Phase 3
0.732	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD5588	Approved
0.731	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7303	Intermediate Similarity	NPD1607	Approved
0.7299	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7585	Approved
0.7294	Intermediate Similarity	NPD7286	Phase 2
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4307	Phase 2
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7279	Intermediate Similarity	NPD1358	Approved
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD1203	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD3226	Approved
0.7262	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2415	Discontinued
0.7243	Intermediate Similarity	NPD7583	Approved
0.7239	Intermediate Similarity	NPD4433	Discontinued
0.7234	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD2532	Approved
0.7233	Intermediate Similarity	NPD2534	Approved
0.7233	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD919	Approved
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2684	Approved
0.7219	Intermediate Similarity	NPD4062	Phase 3
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7178	Intermediate Similarity	NPD6072	Discontinued
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4140	Approved
0.7161	Intermediate Similarity	NPD6032	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7153	Intermediate Similarity	NPD290	Approved
0.7152	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6674	Discontinued
0.7132	Intermediate Similarity	NPD9697	Approved
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD1611	Approved
0.7118	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4666	Phase 3
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5049	Phase 3
0.708	Intermediate Similarity	NPD3134	Approved
0.7078	Intermediate Similarity	NPD6653	Approved
0.7075	Intermediate Similarity	NPD9717	Approved
0.7069	Intermediate Similarity	NPD7685	Pre-registration

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