NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.07
Volume:	273.692
LogP:	3.738
LogD:	2.996
LogS:	-5.746
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.108
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	1.897455149446614e-05
Pgp-inhibitor:	0.068
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	98.03214263916016%
Volume Distribution (VD):	0.441
Pgp-substrate:	1.1951026916503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.497
CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.684
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.403
CYP2D6-substrate:	0.399
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	8.009
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.895
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.181
Carcinogencity:	0.933
Eye Corrosion:	0.005
Eye Irritation:	0.979
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC1268

Natural Product ID:	NPC1268
*Common Name:**	1-Methylchrysophanol
IUPAC Name:	8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	KVRUANCWPQJDMF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O4/c1-8-6-10-14(12(7-8)20-2)16(19)13-9(15(10)18)4-3-5-11(13)17/h3-7,17H,1-2H3
SMILES:	Cc1cc2c(c(c1)OC)C(=O)c1c(cccc1O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454477
PubChem CID:	13412789
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO3206	Karwinskia parvifolia	Species	Rhamnaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25402632]
NPO3206	Karwinskia parvifolia	Species	Rhamnaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[568439]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[568439]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9300.0	nM	PMID[568439]
NPT2	Others	Unspecified		logIC50	=	2.82	n.a.	PMID[568438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[568439]

☑ 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 NPC1268 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	359
0.1-0.2	1630
0.2-0.3	3604
0.3-0.4	9793
0.4-0.5	8774
0.5-0.6	3514
0.6-0.7	7323
0.7-0.8	6314
0.8-0.85	1134
0.85-0.9	220
0.9-0.95	28
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC141934
0.9704	High Similarity	NPC124365
0.9621	High Similarity	NPC1249
0.9357	High Similarity	NPC300540
0.9348	High Similarity	NPC69755
0.9291	High Similarity	NPC56433
0.9291	High Similarity	NPC245584
0.9291	High Similarity	NPC190648
0.9291	High Similarity	NPC126767
0.9291	High Similarity	NPC118027
0.9291	High Similarity	NPC312929
0.9291	High Similarity	NPC289042
0.9242	High Similarity	NPC57552
0.9231	High Similarity	NPC290954
0.9231	High Similarity	NPC255641
0.9167	High Similarity	NPC473201
0.9167	High Similarity	NPC302783
0.9167	High Similarity	NPC282923
0.9097	High Similarity	NPC470568
0.9097	High Similarity	NPC147735
0.9097	High Similarity	NPC294646
0.9078	High Similarity	NPC19896
0.9041	High Similarity	NPC208806
0.9034	High Similarity	NPC470569
0.9014	High Similarity	NPC478019
0.9007	High Similarity	NPC53016
0.8993	High Similarity	NPC26924
0.898	High Similarity	NPC226656
0.898	High Similarity	NPC66508
0.8978	High Similarity	NPC22222
0.8978	High Similarity	NPC281513
0.8973	High Similarity	NPC40356
0.8973	High Similarity	NPC154683
0.8971	High Similarity	NPC115458
0.8963	High Similarity	NPC205992
0.8955	High Similarity	NPC99731
0.8944	High Similarity	NPC193703
0.8944	High Similarity	NPC21599
0.8939	High Similarity	NPC103540
0.8929	High Similarity	NPC315578
0.8912	High Similarity	NPC107109
0.8897	High Similarity	NPC70764
0.8897	High Similarity	NPC70622
0.8897	High Similarity	NPC329933
0.8889	High Similarity	NPC34802
0.8889	High Similarity	NPC71055
0.8881	High Similarity	NPC48248
0.8881	High Similarity	NPC49282
0.8873	High Similarity	NPC167663
0.8864	High Similarity	NPC142956
0.8864	High Similarity	NPC173978
0.8859	High Similarity	NPC178976
0.8841	High Similarity	NPC283088
0.8815	High Similarity	NPC146647
0.8815	High Similarity	NPC34414
0.8811	High Similarity	NPC48762
0.8811	High Similarity	NPC89664
0.8811	High Similarity	NPC274085
0.8803	High Similarity	NPC49108
0.8803	High Similarity	NPC94076
0.8803	High Similarity	NPC182255
0.88	High Similarity	NPC324736
0.8792	High Similarity	NPC14561
0.8792	High Similarity	NPC5379
0.8792	High Similarity	NPC77807
0.8788	High Similarity	NPC375356
0.8784	High Similarity	NPC214632
0.8777	High Similarity	NPC474813
0.8777	High Similarity	NPC272268
0.8776	High Similarity	NPC39819
0.8776	High Similarity	NPC118427
0.8767	High Similarity	NPC80370
0.8759	High Similarity	NPC119767
0.8759	High Similarity	NPC478018
0.8759	High Similarity	NPC309430
0.8759	High Similarity	NPC58685
0.875	High Similarity	NPC136588
0.875	High Similarity	NPC160777
0.875	High Similarity	NPC73416
0.875	High Similarity	NPC475741
0.875	High Similarity	NPC199253
0.875	High Similarity	NPC34482
0.8742	High Similarity	NPC284495
0.8741	High Similarity	NPC84266
0.8741	High Similarity	NPC476473
0.8741	High Similarity	NPC66593
0.8733	High Similarity	NPC199463
0.8733	High Similarity	NPC37543
0.8731	High Similarity	NPC3224
0.8723	High Similarity	NPC470407
0.8716	High Similarity	NPC137125
0.8716	High Similarity	NPC164912
0.8714	High Similarity	NPC245923
0.8712	High Similarity	NPC300274
0.8707	High Similarity	NPC205766
0.8699	High Similarity	NPC472056
0.8699	High Similarity	NPC7025
0.8699	High Similarity	NPC172329
0.8699	High Similarity	NPC5537
0.8699	High Similarity	NPC27221
0.8699	High Similarity	NPC2569
0.8699	High Similarity	NPC256672
0.8696	High Similarity	NPC225051
0.869	High Similarity	NPC470570
0.869	High Similarity	NPC225173
0.869	High Similarity	NPC163846
0.869	High Similarity	NPC147250
0.8686	High Similarity	NPC205360
0.8684	High Similarity	NPC311740
0.8681	High Similarity	NPC475201
0.8681	High Similarity	NPC477409
0.8671	High Similarity	NPC474300
0.8662	High Similarity	NPC472366
0.8658	High Similarity	NPC477691
0.8658	High Similarity	NPC135522
0.8658	High Similarity	NPC329844
0.8652	High Similarity	NPC13715
0.8652	High Similarity	NPC61590
0.8649	High Similarity	NPC258249
0.8649	High Similarity	NPC478148
0.8649	High Similarity	NPC70320
0.8649	High Similarity	NPC149526
0.8649	High Similarity	NPC474417
0.8649	High Similarity	NPC144283
0.8649	High Similarity	NPC230848
0.8647	High Similarity	NPC182646
0.8639	High Similarity	NPC158338
0.8639	High Similarity	NPC288036
0.8639	High Similarity	NPC97029
0.8639	High Similarity	NPC10027
0.8639	High Similarity	NPC65775
0.8639	High Similarity	NPC97028
0.8639	High Similarity	NPC65589
0.8639	High Similarity	NPC100985
0.8633	High Similarity	NPC274876
0.8633	High Similarity	NPC288089
0.863	High Similarity	NPC125801
0.863	High Similarity	NPC7943
0.863	High Similarity	NPC123202
0.863	High Similarity	NPC22005
0.8627	High Similarity	NPC146837
0.8627	High Similarity	NPC278329
0.8621	High Similarity	NPC28632
0.8621	High Similarity	NPC469764
0.8618	High Similarity	NPC476506
0.8618	High Similarity	NPC84571
0.8618	High Similarity	NPC472060
0.8618	High Similarity	NPC472052
0.8618	High Similarity	NPC470342
0.8613	High Similarity	NPC55949
0.8613	High Similarity	NPC31799
0.8611	High Similarity	NPC163948
0.8609	High Similarity	NPC263483
0.8609	High Similarity	NPC44199
0.8601	High Similarity	NPC101366
0.8593	High Similarity	NPC96915
0.8592	High Similarity	NPC223336
0.8592	High Similarity	NPC242994
0.8592	High Similarity	NPC295339
0.8592	High Similarity	NPC477408
0.8592	High Similarity	NPC138099
0.8591	High Similarity	NPC477690
0.8591	High Similarity	NPC3744
0.8591	High Similarity	NPC149889
0.8591	High Similarity	NPC281272
0.8591	High Similarity	NPC312338
0.8582	High Similarity	NPC56332
0.8582	High Similarity	NPC53206
0.8582	High Similarity	NPC305060
0.8582	High Similarity	NPC471905
0.8582	High Similarity	NPC53414
0.8581	High Similarity	NPC202595
0.8571	High Similarity	NPC307174
0.8571	High Similarity	NPC80035
0.8562	High Similarity	NPC469758
0.8561	High Similarity	NPC254603
0.8561	High Similarity	NPC53896
0.8561	High Similarity	NPC470406
0.8561	High Similarity	NPC314048
0.8561	High Similarity	NPC52407
0.8551	High Similarity	NPC244699
0.8551	High Similarity	NPC474517
0.8551	High Similarity	NPC72669
0.8551	High Similarity	NPC301717
0.8543	High Similarity	NPC279605
0.8543	High Similarity	NPC478223
0.8542	High Similarity	NPC232021
0.8542	High Similarity	NPC201297
0.8542	High Similarity	NPC26051
0.8542	High Similarity	NPC126534
0.8542	High Similarity	NPC55832
0.8542	High Similarity	NPC40118
0.8542	High Similarity	NPC268204
0.8542	High Similarity	NPC52789
0.8533	High Similarity	NPC169990
0.8533	High Similarity	NPC93552
0.8533	High Similarity	NPC210942
0.8531	High Similarity	NPC477956
0.8531	High Similarity	NPC109232
0.8531	High Similarity	NPC181560

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 NPC1268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	979
0.2-0.3	1321
0.3-0.4	2491
0.4-0.5	2097
0.5-0.6	1221
0.6-0.7	513
0.7-0.8	163
0.8-0.85	16
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD3226	Approved
0.8939	High Similarity	NPD1470	Approved
0.8786	High Similarity	NPD2346	Discontinued
0.8636	High Similarity	NPD1201	Approved
0.8511	High Similarity	NPD1509	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6232	Discontinued
0.8369	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8252	Intermediate Similarity	NPD1510	Phase 2
0.8227	Intermediate Similarity	NPD1240	Approved
0.8214	Intermediate Similarity	NPD2313	Discontinued
0.8188	Intermediate Similarity	NPD2798	Approved
0.817	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD2799	Discontinued
0.8121	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7003	Approved
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8069	Intermediate Similarity	NPD5408	Approved
0.8069	Intermediate Similarity	NPD5406	Approved
0.8069	Intermediate Similarity	NPD5405	Approved
0.8069	Intermediate Similarity	NPD5404	Approved
0.8045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2344	Approved
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3750	Approved
0.7959	Intermediate Similarity	NPD1549	Phase 2
0.7959	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3764	Approved
0.7945	Intermediate Similarity	NPD1551	Phase 2
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1283	Approved
0.7908	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD8313	Approved
0.7879	Intermediate Similarity	NPD8312	Approved
0.7868	Intermediate Similarity	NPD1651	Approved
0.7857	Intermediate Similarity	NPD4380	Phase 2
0.7834	Intermediate Similarity	NPD7768	Phase 2
0.7826	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7390	Discontinued
0.7806	Intermediate Similarity	NPD7411	Suspended
0.78	Intermediate Similarity	NPD2309	Approved
0.7786	Intermediate Similarity	NPD1876	Approved
0.7785	Intermediate Similarity	NPD3749	Approved
0.777	Intermediate Similarity	NPD1471	Phase 3
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1934	Approved
0.7751	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1203	Approved
0.7707	Intermediate Similarity	NPD2801	Approved
0.7703	Intermediate Similarity	NPD2796	Approved
0.7698	Intermediate Similarity	NPD1281	Approved
0.7697	Intermediate Similarity	NPD1511	Approved
0.7681	Intermediate Similarity	NPD4626	Approved
0.7677	Intermediate Similarity	NPD7458	Discontinued
0.7673	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3972	Approved
0.7639	Intermediate Similarity	NPD4625	Phase 3
0.7635	Intermediate Similarity	NPD3748	Approved
0.7635	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD7177	Discontinued
0.7616	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.761	Intermediate Similarity	NPD3882	Suspended
0.7607	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD411	Approved
0.7584	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.755	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD1608	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7518	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7484	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD943	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7465	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6782	Approved
0.7458	Intermediate Similarity	NPD6779	Approved
0.7458	Intermediate Similarity	NPD6777	Approved
0.7458	Intermediate Similarity	NPD6778	Approved
0.7458	Intermediate Similarity	NPD6776	Approved
0.7458	Intermediate Similarity	NPD6781	Approved
0.7458	Intermediate Similarity	NPD6780	Approved
0.7448	Intermediate Similarity	NPD6832	Phase 2
0.7438	Intermediate Similarity	NPD5402	Approved
0.7432	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD447	Suspended
0.7427	Intermediate Similarity	NPD8150	Discontinued
0.7421	Intermediate Similarity	NPD6801	Discontinued
0.7419	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6651	Approved
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD4307	Phase 2
0.7365	Intermediate Similarity	NPD2979	Phase 3
0.7361	Intermediate Similarity	NPD1164	Approved
0.7361	Intermediate Similarity	NPD2797	Approved
0.7357	Intermediate Similarity	NPD5691	Approved
0.7355	Intermediate Similarity	NPD6799	Approved
0.7347	Intermediate Similarity	NPD3268	Approved
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7697	Approved
0.7333	Intermediate Similarity	NPD7698	Approved
0.7333	Intermediate Similarity	NPD7696	Phase 3
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.7325	Intermediate Similarity	NPD5403	Approved
0.7312	Intermediate Similarity	NPD6844	Discontinued
0.7308	Intermediate Similarity	NPD5401	Approved
0.7305	Intermediate Similarity	NPD3019	Approved
0.7305	Intermediate Similarity	NPD17	Approved
0.7305	Intermediate Similarity	NPD3818	Discontinued
0.7293	Intermediate Similarity	NPD7871	Phase 2
0.7293	Intermediate Similarity	NPD7870	Phase 2
0.729	Intermediate Similarity	NPD3300	Phase 2
0.7284	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD6823	Phase 2
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7246	Intermediate Similarity	NPD5951	Approved
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2342	Discontinued
0.723	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2296	Approved
0.7222	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD1243	Approved
0.7205	Intermediate Similarity	NPD37	Approved
0.7203	Intermediate Similarity	NPD1611	Approved
0.7202	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD1933	Approved
0.7183	Intermediate Similarity	NPD2932	Approved
0.7183	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6535	Approved
0.7175	Intermediate Similarity	NPD6534	Approved
0.7174	Intermediate Similarity	NPD7701	Phase 2
0.7172	Intermediate Similarity	NPD6696	Suspended
0.7171	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7033	Discontinued
0.7163	Intermediate Similarity	NPD9545	Approved
0.7162	Intermediate Similarity	NPD7008	Discontinued
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7124	Intermediate Similarity	NPD2438	Suspended
0.7124	Intermediate Similarity	NPD4477	Approved
0.7124	Intermediate Similarity	NPD2531	Phase 2
0.7124	Intermediate Similarity	NPD4476	Approved
0.7123	Intermediate Similarity	NPD3266	Approved
0.7123	Intermediate Similarity	NPD3267	Approved
0.7119	Intermediate Similarity	NPD6212	Phase 3
0.7119	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6213	Phase 3
0.7118	Intermediate Similarity	NPD7074	Phase 3
0.7115	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD7874	Approved
0.7097	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4908	Phase 1
0.7093	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4967	Phase 2
0.7073	Intermediate Similarity	NPD4966	Approved
0.7073	Intermediate Similarity	NPD4965	Approved
0.707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8032	Phase 2
0.7063	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7801	Approved
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD7700	Phase 2
0.7056	Intermediate Similarity	NPD7699	Phase 2

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