NPASS Compound

Structure

NPC474203 OpenBabel07101719522D 37 42 0 0 1 0 0 0 0 0999 V2000 -4.3301 -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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 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 -2.5981 -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 2.5000 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 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 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 -0.8660 -1.5000 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 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 5 19 2 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 20 2 0 0 0 0 9 13 1 0 0 0 0 9 21 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 22 2 0 0 0 0 14 31 1 0 0 0 0 15 25 2 0 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 27 2 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 25 1 0 0 0 0 19 32 1 0 0 0 0 20 26 1 0 0 0 0 20 33 1 0 0 0 0 21 27 1 0 0 0 0 21 34 1 0 0 0 0 22 28 1 0 0 0 0 22 35 1 0 0 0 0 23 15 1 1 0 0 0 23 24 1 0 0 0 0 24 17 1 1 0 0 0 25 29 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 30 1 0 0 0 0 29 36 2 0 0 0 0 30 37 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.14
Volume:	500.718
LogP:	7.143
LogD:	3.169
LogS:	-4.725
# Rotatable Bonds:	1
TPSA:	141.61
# H-Bond Aceptor:	7
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	2.977
Fsp3:	0.067
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.0
MDCK Permeability:	6.244208634598181e-06
Pgp-inhibitor:	0.14
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.485
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	92.92867279052734%
Volume Distribution (VD):	0.32
Pgp-substrate:	9.701711654663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	5.395
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.962
Carcinogencity:	0.044
Eye Corrosion:	0.004
Eye Irritation:	0.952
Respiratory Toxicity:	0.119

Download Data

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

Natural Product: NPC474203

Natural Product ID:	NPC474203
*Common Name:**	(9R,9'r)-2,4,4',5,5'-Pentahydroxy-2',7-Dimethyl-9,9'-Bianthracene-10,10'(9H,9'h)-Dione
IUPAC Name:	(10R)-10-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one
Synonyms:
Standard InCHIKey:	VUUFXTUVVIEIMH-DNQXCXABSA-N
Standard InCHI:	InChI=1S/C30H22O7/c1-12-6-16-23(15-4-3-5-19(32)25(15)29(36)26(16)20(33)8-12)24-17-7-13(2)9-21(34)27(17)30(37)28-18(24)10-14(31)11-22(28)35/h3-11,23-24,31-35H,1-2H3/t23-,24-/m1/s1
SMILES:	CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C5=C(C(=CC(=C5)C)O)C(=O)C6=C4C=C(C=C6O)O)C=CC=C3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463459
PubChem CID:	44567181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO32935	rhamnus nepalensis	Species	Rhamnaceae	Eukaryota	Leaves	Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam	1995-Nov	PMID[11575949]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3400.0	nM	PMID[514088]

☑ 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 NPC474203 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	405
0.1-0.2	1743
0.2-0.3	3834
0.3-0.4	10585
0.4-0.5	8467
0.5-0.6	5231
0.6-0.7	6416
0.7-0.8	5155
0.8-0.85	653
0.85-0.9	156
0.9-0.95	46
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295712
1.0	High Similarity	NPC451542
1.0	High Similarity	NPC313047
0.9854	High Similarity	NPC293545
0.9854	High Similarity	NPC174905
0.964	High Similarity	NPC227841
0.9568	High Similarity	NPC296752
0.9441	High Similarity	NPC477221
0.9437	High Similarity	NPC37709
0.9437	High Similarity	NPC290194
0.9433	High Similarity	NPC12402
0.9366	High Similarity	NPC271944
0.9366	High Similarity	NPC110882
0.9366	High Similarity	NPC85393
0.9353	High Similarity	NPC169452
0.9353	High Similarity	NPC181560
0.9343	High Similarity	NPC191976
0.9338	High Similarity	NPC472262
0.9338	High Similarity	NPC287604
0.9338	High Similarity	NPC161964
0.9286	High Similarity	NPC246638
0.9281	High Similarity	NPC138099
0.9281	High Similarity	NPC242994
0.9265	High Similarity	NPC267205
0.9225	High Similarity	NPC10764
0.922	High Similarity	NPC19631
0.922	High Similarity	NPC193555
0.922	High Similarity	NPC239136
0.9155	High Similarity	NPC471682
0.9137	High Similarity	NPC53414
0.9137	High Similarity	NPC53206
0.9137	High Similarity	NPC471905
0.9085	High Similarity	NPC257644
0.9065	High Similarity	NPC118919
0.9065	High Similarity	NPC254847
0.9058	High Similarity	NPC166480
0.9058	High Similarity	NPC282780
0.9051	High Similarity	NPC175738
0.9048	High Similarity	NPC35
0.9028	High Similarity	NPC471683
0.9	High Similarity	NPC474110
0.9	High Similarity	NPC44960
0.8978	High Similarity	NPC72669
0.8978	High Similarity	NPC474517
0.8971	High Similarity	NPC92624
0.8951	High Similarity	NPC135524
0.8951	High Similarity	NPC474961
0.8936	High Similarity	NPC20210
0.8921	High Similarity	NPC44437
0.8905	High Similarity	NPC259942
0.8881	High Similarity	NPC204045
0.8881	High Similarity	NPC305845
0.8873	High Similarity	NPC143438
0.8865	High Similarity	NPC53001
0.8865	High Similarity	NPC62272
0.8857	High Similarity	NPC290803
0.8832	High Similarity	NPC109123
0.8828	High Similarity	NPC21599
0.8828	High Similarity	NPC193703
0.8819	High Similarity	NPC85310
0.8811	High Similarity	NPC225243
0.8803	High Similarity	NPC473622
0.8803	High Similarity	NPC13715
0.8803	High Similarity	NPC87723
0.8786	High Similarity	NPC12070
0.8784	High Similarity	NPC329933
0.8767	High Similarity	NPC34482
0.8759	High Similarity	NPC473017
0.8758	High Similarity	NPC472060
0.8758	High Similarity	NPC472052
0.8758	High Similarity	NPC470342
0.875	High Similarity	NPC106519
0.875	High Similarity	NPC267846
0.875	High Similarity	NPC91019
0.8742	High Similarity	NPC66508
0.8742	High Similarity	NPC226656
0.8741	High Similarity	NPC190457
0.8741	High Similarity	NPC162939
0.8725	High Similarity	NPC205766
0.8723	High Similarity	NPC249272
0.8723	High Similarity	NPC283088
0.8714	High Similarity	NPC114183
0.8714	High Similarity	NPC180261
0.8714	High Similarity	NPC225051
0.8714	High Similarity	NPC37299
0.8707	High Similarity	NPC470570
0.8701	High Similarity	NPC18380
0.8699	High Similarity	NPC471906
0.8699	High Similarity	NPC244691
0.8699	High Similarity	NPC48762
0.8696	High Similarity	NPC474998
0.8693	High Similarity	NPC195167
0.8693	High Similarity	NPC177650
0.869	High Similarity	NPC137649
0.869	High Similarity	NPC73061
0.8686	High Similarity	NPC266689
0.8686	High Similarity	NPC100067
0.8686	High Similarity	NPC169250
0.8686	High Similarity	NPC116513
0.8686	High Similarity	NPC103356
0.8686	High Similarity	NPC72158
0.8686	High Similarity	NPC98254
0.8686	High Similarity	NPC162612
0.8686	High Similarity	NPC190043
0.8686	High Similarity	NPC23126
0.8686	High Similarity	NPC30501
0.8686	High Similarity	NPC105157
0.8676	High Similarity	NPC477454
0.8652	High Similarity	NPC475088
0.8652	High Similarity	NPC270899
0.8649	High Similarity	NPC34802
0.8649	High Similarity	NPC261271
0.8649	High Similarity	NPC475348
0.8636	High Similarity	NPC312993
0.8636	High Similarity	NPC186325
0.8636	High Similarity	NPC292863
0.8636	High Similarity	NPC184326
0.8623	High Similarity	NPC21305
0.8623	High Similarity	NPC221777
0.8621	High Similarity	NPC110810
0.8621	High Similarity	NPC187843
0.8621	High Similarity	NPC290550
0.8621	High Similarity	NPC477275
0.8618	High Similarity	NPC254351
0.8613	High Similarity	NPC473691
0.8613	High Similarity	NPC160499
0.8613	High Similarity	NPC62952
0.8603	High Similarity	NPC173978
0.8601	High Similarity	NPC245923
0.8601	High Similarity	NPC290030
0.8592	High Similarity	NPC80035
0.8591	High Similarity	NPC152233
0.8582	High Similarity	NPC48036
0.8582	High Similarity	NPC115458
0.8581	High Similarity	NPC273467
0.8581	High Similarity	NPC137232
0.8581	High Similarity	NPC143685
0.8581	High Similarity	NPC189552
0.8571	High Similarity	NPC55443
0.8571	High Similarity	NPC324736
0.8571	High Similarity	NPC18699
0.8562	High Similarity	NPC469520
0.8562	High Similarity	NPC26238
0.8561	High Similarity	NPC99731
0.8561	High Similarity	NPC276238
0.8553	High Similarity	NPC329844
0.8552	High Similarity	NPC203063
0.8542	High Similarity	NPC4214
0.854	High Similarity	NPC475733
0.8531	High Similarity	NPC155211
0.8531	High Similarity	NPC264112
0.8531	High Similarity	NPC194764
0.8531	High Similarity	NPC65005
0.8531	High Similarity	NPC474813
0.8529	High Similarity	NPC472029
0.8529	High Similarity	NPC65761
0.8526	High Similarity	NPC15374
0.8523	High Similarity	NPC245584
0.8523	High Similarity	NPC162751
0.8523	High Similarity	NPC126767
0.8523	High Similarity	NPC190648
0.8523	High Similarity	NPC289042
0.8523	High Similarity	NPC52161
0.8523	High Similarity	NPC56433
0.8523	High Similarity	NPC312929
0.8523	High Similarity	NPC118027
0.8521	High Similarity	NPC50924
0.8521	High Similarity	NPC474519
0.8511	High Similarity	NPC58685
0.8506	High Similarity	NPC317580
0.8503	High Similarity	NPC84266
0.85	High Similarity	NPC247477
0.85	High Similarity	NPC62219
0.85	High Similarity	NPC17840
0.8497	Intermediate Similarity	NPC66029
0.8497	Intermediate Similarity	NPC318270
0.8489	Intermediate Similarity	NPC96024
0.8489	Intermediate Similarity	NPC282923
0.8489	Intermediate Similarity	NPC48248
0.8483	Intermediate Similarity	NPC472903
0.8481	Intermediate Similarity	NPC477835
0.8478	Intermediate Similarity	NPC8745
0.8477	Intermediate Similarity	NPC470568
0.8477	Intermediate Similarity	NPC255641
0.8477	Intermediate Similarity	NPC290954
0.8471	Intermediate Similarity	NPC290160
0.8467	Intermediate Similarity	NPC13238
0.8467	Intermediate Similarity	NPC106524
0.8467	Intermediate Similarity	NPC199273
0.8467	Intermediate Similarity	NPC290695
0.8462	Intermediate Similarity	NPC161632
0.8456	Intermediate Similarity	NPC91105
0.8456	Intermediate Similarity	NPC225173
0.8456	Intermediate Similarity	NPC314437
0.8456	Intermediate Similarity	NPC163846
0.8452	Intermediate Similarity	NPC326084
0.8451	Intermediate Similarity	NPC40524
0.8451	Intermediate Similarity	NPC213485
0.8451	Intermediate Similarity	NPC139074
0.8442	Intermediate Similarity	NPC56049

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 NPC474203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	974
0.2-0.3	1406
0.3-0.4	2885
0.4-0.5	2072
0.5-0.6	1024
0.6-0.7	305
0.7-0.8	94
0.8-0.85	8
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.964	High Similarity	NPD7390	Discontinued
0.9065	High Similarity	NPD1509	Clinical (unspecified phase)
0.8865	High Similarity	NPD5404	Approved
0.8865	High Similarity	NPD5406	Approved
0.8865	High Similarity	NPD5408	Approved
0.8865	High Similarity	NPD5405	Approved
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8382	Intermediate Similarity	NPD1201	Approved
0.8273	Intermediate Similarity	NPD1470	Approved
0.8267	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD943	Approved
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8026	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1607	Approved
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7819	Suspended
0.7785	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1510	Phase 2
0.7763	Intermediate Similarity	NPD7003	Approved
0.7755	Intermediate Similarity	NPD1240	Approved
0.775	Intermediate Similarity	NPD7768	Phase 2
0.7748	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7411	Suspended
0.7702	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD2534	Approved
0.7677	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD4380	Phase 2
0.7589	Intermediate Similarity	NPD3019	Approved
0.7566	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3300	Phase 2
0.7532	Intermediate Similarity	NPD3750	Approved
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1164	Approved
0.7516	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7465	Intermediate Similarity	NPD2932	Approved
0.7453	Intermediate Similarity	NPD1934	Approved
0.7434	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2801	Approved
0.7405	Intermediate Similarity	NPD1512	Approved
0.7396	Intermediate Similarity	NPD6020	Phase 2
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD2796	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7303	Intermediate Similarity	NPD6651	Approved
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4750	Phase 3
0.7289	Intermediate Similarity	NPD5494	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8150	Discontinued
0.7256	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2800	Approved
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7212	Intermediate Similarity	NPD3882	Suspended
0.7208	Intermediate Similarity	NPD3748	Approved
0.7208	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD8166	Discontinued
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3026	Approved
0.7172	Intermediate Similarity	NPD3023	Approved
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7153	Intermediate Similarity	NPD3024	Approved
0.7153	Intermediate Similarity	NPD2342	Discontinued
0.7153	Intermediate Similarity	NPD3025	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD2344	Approved
0.7114	Intermediate Similarity	NPD2798	Approved
0.7111	Intermediate Similarity	NPD6534	Approved
0.7111	Intermediate Similarity	NPD6535	Approved
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5710	Approved
0.7101	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD7054	Approved
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7074	Intermediate Similarity	NPD8151	Discontinued
0.7063	Intermediate Similarity	NPD6799	Approved
0.7052	Intermediate Similarity	NPD7472	Approved
0.7051	Intermediate Similarity	NPD1551	Phase 2
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7043	Intermediate Similarity	NPD7871	Phase 2
0.7043	Intermediate Similarity	NPD7870	Phase 2
0.7042	Intermediate Similarity	NPD5951	Approved
0.7035	Intermediate Similarity	NPD7177	Discontinued
0.7029	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7635	Approved
0.702	Intermediate Similarity	NPD4908	Phase 1
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6779	Approved
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7011	Intermediate Similarity	NPD6777	Approved
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6986	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1283	Approved
0.6971	Remote Similarity	NPD7251	Discontinued
0.6959	Remote Similarity	NPD9269	Phase 2
0.6952	Remote Similarity	NPD8320	Phase 1
0.6952	Remote Similarity	NPD8319	Approved
0.6937	Remote Similarity	NPD2309	Approved
0.6936	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7808	Phase 3
0.6918	Remote Similarity	NPD9268	Approved
0.6918	Remote Similarity	NPD1243	Approved
0.6918	Remote Similarity	NPD1651	Approved
0.6912	Remote Similarity	NPD940	Approved
0.6912	Remote Similarity	NPD846	Approved
0.6901	Remote Similarity	NPD7229	Phase 3
0.6898	Remote Similarity	NPD7696	Phase 3
0.6898	Remote Similarity	NPD7435	Discontinued
0.6898	Remote Similarity	NPD7698	Approved
0.6898	Remote Similarity	NPD7697	Approved
0.6886	Remote Similarity	NPD1465	Phase 2
0.6883	Remote Similarity	NPD6663	Approved
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6273	Approved
0.6868	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6212	Phase 3
0.6868	Remote Similarity	NPD6213	Phase 3
0.6857	Remote Similarity	NPD74	Approved
0.6857	Remote Similarity	NPD9266	Approved
0.6846	Remote Similarity	NPD3972	Approved
0.6842	Remote Similarity	NPD5736	Approved
0.6838	Remote Similarity	NPD1242	Phase 1
0.6828	Remote Similarity	NPD9493	Approved
0.6826	Remote Similarity	NPD37	Approved
0.6818	Remote Similarity	NPD5953	Discontinued
0.6818	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.6796	Remote Similarity	NPD4287	Approved
0.6795	Remote Similarity	NPD230	Phase 1
0.6786	Remote Similarity	NPD9263	Approved
0.6786	Remote Similarity	NPD9267	Approved
0.6786	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9264	Approved
0.6779	Remote Similarity	NPD1281	Approved
0.677	Remote Similarity	NPD4628	Phase 3
0.6765	Remote Similarity	NPD3020	Approved
0.6763	Remote Similarity	NPD3926	Phase 2
0.6757	Remote Similarity	NPD2286	Discontinued
0.6757	Remote Similarity	NPD4626	Approved
0.6755	Remote Similarity	NPD6823	Phase 2
0.6754	Remote Similarity	NPD7701	Phase 2
0.6753	Remote Similarity	NPD7008	Discontinued
0.6746	Remote Similarity	NPD5402	Approved
0.6744	Remote Similarity	NPD7199	Phase 2
0.6742	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4360	Phase 2
0.6739	Remote Similarity	NPD4363	Phase 3
0.6738	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7801	Approved
0.6735	Remote Similarity	NPD3091	Approved
0.6733	Remote Similarity	NPD4878	Approved
0.6727	Remote Similarity	NPD920	Approved
0.6727	Remote Similarity	NPD5403	Approved
0.6725	Remote Similarity	NPD6234	Discontinued
0.6711	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.6711	Remote Similarity	NPD3094	Phase 2
0.6706	Remote Similarity	NPD4965	Approved
0.6706	Remote Similarity	NPD4967	Phase 2
0.6706	Remote Similarity	NPD4966	Approved
0.6705	Remote Similarity	NPD7286	Phase 2
0.6705	Remote Similarity	NPD3787	Discontinued
0.669	Remote Similarity	NPD3022	Approved
0.669	Remote Similarity	NPD3021	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