NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.06
Volume:	241.737
LogP:	2.498
LogD:	2.484
LogS:	-3.954
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.257
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.746
MDCK Permeability:	1.5114465895749163e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	94.62177276611328%
Volume Distribution (VD):	0.795
Pgp-substrate:	3.709702253341675%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.138
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.636
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	11.819
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.609
Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.111
Carcinogencity:	0.145
Eye Corrosion:	0.005
Eye Irritation:	0.947
Respiratory Toxicity:	0.168

Download Data

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

Natural Product: NPC103752

Natural Product ID:	NPC103752
*Common Name:**	Nobilone
IUPAC Name:	2,7-dihydroxy-4-methoxyfluoren-9-one
Synonyms:	Nobilone
Standard InCHIKey:	GLMNDDJSYQXNSY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c1-18-12-6-8(16)5-11-13(12)9-3-2-7(15)4-10(9)14(11)17/h2-6,15-16H,1H3
SMILES:	COc1cc(cc2c1-c1ccc(cc1C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL385256
PubChem CID:	16104871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3894	Dendrobium nobile	Species	Orchidaceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2735	Cell Line	RAW	Mus musculus	IC50	=	38100.0	nM	PMID[483340]
NPT1	Others	Radical scavenging activity		IC50	>	200000.0	nM	PMID[483340]

☑ 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 NPC103752 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	399
0.1-0.2	1722
0.2-0.3	3806
0.3-0.4	10323
0.4-0.5	8003
0.5-0.6	3317
0.6-0.7	6220
0.7-0.8	6764
0.8-0.85	1791
0.85-0.9	319
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC18714
0.9574	High Similarity	NPC216624
0.9286	High Similarity	NPC49108
0.9116	High Similarity	NPC303950
0.9021	High Similarity	NPC19896
0.9014	High Similarity	NPC94076
0.9014	High Similarity	NPC182255
0.898	High Similarity	NPC115324
0.8978	High Similarity	NPC309717
0.8978	High Similarity	NPC189106
0.8978	High Similarity	NPC112192
0.8978	High Similarity	NPC164236
0.8978	High Similarity	NPC66384
0.8978	High Similarity	NPC128348
0.8973	High Similarity	NPC80370
0.8971	High Similarity	NPC247779
0.8951	High Similarity	NPC84266
0.8936	High Similarity	NPC472368
0.8929	High Similarity	NPC476333
0.8929	High Similarity	NPC472367
0.8929	High Similarity	NPC24394
0.8929	High Similarity	NPC473391
0.8929	High Similarity	NPC472364
0.8919	High Similarity	NPC207624
0.8882	High Similarity	NPC96031
0.8881	High Similarity	NPC250755
0.8873	High Similarity	NPC472366
0.8865	High Similarity	NPC23870
0.8865	High Similarity	NPC212767
0.8851	High Similarity	NPC78505
0.8851	High Similarity	NPC230848
0.8851	High Similarity	NPC58668
0.8851	High Similarity	NPC23668
0.8851	High Similarity	NPC193976
0.8851	High Similarity	NPC106372
0.8849	High Similarity	NPC27643
0.8841	High Similarity	NPC313618
0.8836	High Similarity	NPC77903
0.8836	High Similarity	NPC56433
0.8836	High Similarity	NPC190648
0.8836	High Similarity	NPC17101
0.8836	High Similarity	NPC245584
0.8836	High Similarity	NPC126767
0.8836	High Similarity	NPC289042
0.8836	High Similarity	NPC312929
0.8836	High Similarity	NPC118027
0.8828	High Similarity	NPC131766
0.8819	High Similarity	NPC287722
0.8819	High Similarity	NPC310340
0.8811	High Similarity	NPC275734
0.8803	High Similarity	NPC55162
0.8803	High Similarity	NPC12175
0.8803	High Similarity	NPC278323
0.8803	High Similarity	NPC309154
0.8803	High Similarity	NPC90665
0.8803	High Similarity	NPC279668
0.88	High Similarity	NPC148938
0.8794	High Similarity	NPC193792
0.8794	High Similarity	NPC87545
0.8794	High Similarity	NPC213603
0.8794	High Similarity	NPC235428
0.8792	High Similarity	NPC142308
0.8786	High Similarity	NPC286336
0.8784	High Similarity	NPC290954
0.8784	High Similarity	NPC255641
0.8784	High Similarity	NPC470107
0.8777	High Similarity	NPC212631
0.8777	High Similarity	NPC205468
0.8777	High Similarity	NPC257756
0.8777	High Similarity	NPC87231
0.8777	High Similarity	NPC129132
0.8776	High Similarity	NPC172329
0.8776	High Similarity	NPC2569
0.8759	High Similarity	NPC475201
0.8759	High Similarity	NPC105213
0.8759	High Similarity	NPC207732
0.875	High Similarity	NPC312256
0.8741	High Similarity	NPC477956
0.8741	High Similarity	NPC109232
0.8733	High Similarity	NPC235333
0.8732	High Similarity	NPC472419
0.8732	High Similarity	NPC294409
0.8732	High Similarity	NPC303644
0.8732	High Similarity	NPC162680
0.8732	High Similarity	NPC7013
0.8732	High Similarity	NPC116632
0.8732	High Similarity	NPC209560
0.8732	High Similarity	NPC181124
0.8725	High Similarity	NPC272566
0.8725	High Similarity	NPC258249
0.8723	High Similarity	NPC39426
0.8723	High Similarity	NPC234560
0.8716	High Similarity	NPC65775
0.8716	High Similarity	NPC329933
0.8716	High Similarity	NPC10027
0.8714	High Similarity	NPC192304
0.8714	High Similarity	NPC175098
0.8714	High Similarity	NPC82225
0.8714	High Similarity	NPC263670
0.8714	High Similarity	NPC28753
0.8714	High Similarity	NPC56031
0.8714	High Similarity	NPC472365
0.8714	High Similarity	NPC144051
0.8714	High Similarity	NPC20560
0.8714	High Similarity	NPC18877
0.8714	High Similarity	NPC188646
0.8714	High Similarity	NPC242294
0.8714	High Similarity	NPC159623
0.8714	High Similarity	NPC204960
0.8714	High Similarity	NPC294593
0.8714	High Similarity	NPC139813
0.8714	High Similarity	NPC312318
0.8714	High Similarity	NPC337373
0.8707	High Similarity	NPC34802
0.8707	High Similarity	NPC17816
0.8707	High Similarity	NPC7943
0.8707	High Similarity	NPC22005
0.8707	High Similarity	NPC123202
0.8705	High Similarity	NPC64359
0.8705	High Similarity	NPC262359
0.8705	High Similarity	NPC308037
0.8699	High Similarity	NPC98926
0.8699	High Similarity	NPC230943
0.8699	High Similarity	NPC155144
0.869	High Similarity	NPC53192
0.8684	High Similarity	NPC164110
0.8684	High Similarity	NPC246647
0.8684	High Similarity	NPC96342
0.8684	High Similarity	NPC212967
0.8681	High Similarity	NPC110419
0.8681	High Similarity	NPC11056
0.8681	High Similarity	NPC101366
0.8675	High Similarity	NPC99199
0.8675	High Similarity	NPC213936
0.8675	High Similarity	NPC297531
0.8675	High Similarity	NPC226656
0.8675	High Similarity	NPC66508
0.8671	High Similarity	NPC21350
0.8667	High Similarity	NPC28103
0.8662	High Similarity	NPC477242
0.8662	High Similarity	NPC249606
0.8662	High Similarity	NPC274109
0.8662	High Similarity	NPC66349
0.8662	High Similarity	NPC1486
0.8662	High Similarity	NPC168105
0.8662	High Similarity	NPC477243
0.8662	High Similarity	NPC150399
0.8662	High Similarity	NPC477244
0.8662	High Similarity	NPC186838
0.8662	High Similarity	NPC41461
0.8662	High Similarity	NPC12165
0.8662	High Similarity	NPC98115
0.8662	High Similarity	NPC25287
0.8658	High Similarity	NPC13282
0.8658	High Similarity	NPC119929
0.8658	High Similarity	NPC294646
0.8658	High Similarity	NPC147735
0.8658	High Similarity	NPC470568
0.8658	High Similarity	NPC85131
0.8658	High Similarity	NPC295036
0.8652	High Similarity	NPC182496
0.8652	High Similarity	NPC180905
0.8649	High Similarity	NPC256672
0.8649	High Similarity	NPC27221
0.8649	High Similarity	NPC472841
0.8649	High Similarity	NPC7025
0.8639	High Similarity	NPC267509
0.8639	High Similarity	NPC138978
0.8639	High Similarity	NPC163846
0.8639	High Similarity	NPC225173
0.863	High Similarity	NPC302181
0.8621	High Similarity	NPC232021
0.8621	High Similarity	NPC126534
0.8621	High Similarity	NPC284556
0.8621	High Similarity	NPC52789
0.8621	High Similarity	NPC26051
0.8621	High Similarity	NPC40118
0.8621	High Similarity	NPC301178
0.8621	High Similarity	NPC268204
0.8621	High Similarity	NPC55832
0.8618	High Similarity	NPC180924
0.8611	High Similarity	NPC254994
0.8611	High Similarity	NPC295384
0.8609	High Similarity	NPC208806
0.8601	High Similarity	NPC153979
0.8601	High Similarity	NPC317119
0.8601	High Similarity	NPC470962
0.86	High Similarity	NPC170169
0.86	High Similarity	NPC470569
0.8592	High Similarity	NPC13575
0.8592	High Similarity	NPC242712
0.8592	High Similarity	NPC156092
0.8592	High Similarity	NPC131039
0.8591	High Similarity	NPC97028
0.8591	High Similarity	NPC288036
0.8591	High Similarity	NPC65589
0.8591	High Similarity	NPC158338
0.8591	High Similarity	NPC97029
0.8591	High Similarity	NPC100985
0.8581	High Similarity	NPC125801

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 NPC103752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	990
0.2-0.3	1469
0.3-0.4	2594
0.4-0.5	1964
0.5-0.6	1131
0.6-0.7	447
0.7-0.8	153
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD1240	Approved
0.8723	High Similarity	NPD1510	Phase 2
0.8714	High Similarity	NPD1607	Approved
0.8542	High Similarity	NPD970	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3750	Approved
0.8414	Intermediate Similarity	NPD1549	Phase 2
0.8345	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7819	Suspended
0.8207	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3749	Approved
0.82	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3882	Suspended
0.8133	Intermediate Similarity	NPD1511	Approved
0.8129	Intermediate Similarity	NPD1876	Approved
0.8113	Intermediate Similarity	NPD6232	Discontinued
0.8082	Intermediate Similarity	NPD3748	Approved
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8075	Intermediate Similarity	NPD7473	Discontinued
0.8065	Intermediate Similarity	NPD1934	Approved
0.8056	Intermediate Similarity	NPD943	Approved
0.8027	Intermediate Similarity	NPD2796	Approved
0.8026	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1465	Phase 2
0.8013	Intermediate Similarity	NPD2801	Approved
0.7973	Intermediate Similarity	NPD2344	Approved
0.7961	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6959	Discontinued
0.7935	Intermediate Similarity	NPD4380	Phase 2
0.7905	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD2800	Approved
0.7848	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3764	Approved
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6799	Approved
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7763	Intermediate Similarity	NPD2309	Approved
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD230	Phase 1
0.775	Intermediate Similarity	NPD7075	Discontinued
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1243	Approved
0.7742	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD920	Approved
0.7718	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6599	Discontinued
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD1470	Approved
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7683	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7390	Discontinued
0.7654	Intermediate Similarity	NPD5494	Approved
0.7643	Intermediate Similarity	NPD3226	Approved
0.764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1283	Approved
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7613	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7199	Phase 2
0.7606	Intermediate Similarity	NPD1608	Approved
0.7606	Intermediate Similarity	NPD3972	Approved
0.7597	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6651	Approved
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6166	Phase 2
0.7571	Intermediate Similarity	NPD1651	Approved
0.7535	Intermediate Similarity	NPD1610	Phase 2
0.7535	Intermediate Similarity	NPD1201	Approved
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD919	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD7003	Approved
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD9494	Approved
0.7455	Intermediate Similarity	NPD7229	Phase 3
0.7455	Intermediate Similarity	NPD5710	Approved
0.7455	Intermediate Similarity	NPD5711	Approved
0.7448	Intermediate Similarity	NPD1203	Approved
0.7415	Intermediate Similarity	NPD4908	Phase 1
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7413	Intermediate Similarity	NPD1281	Approved
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD4288	Approved
0.7397	Intermediate Similarity	NPD2798	Approved
0.7396	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD17	Approved
0.7391	Intermediate Similarity	NPD37	Approved
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7357	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5953	Discontinued
0.7342	Intermediate Similarity	NPD6273	Approved
0.7337	Intermediate Similarity	NPD7054	Approved
0.7325	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5408	Approved
0.732	Intermediate Similarity	NPD5404	Approved
0.732	Intermediate Similarity	NPD5405	Approved
0.732	Intermediate Similarity	NPD5406	Approved
0.7315	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3268	Approved
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5402	Approved
0.7297	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7472	Approved
0.729	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4965	Approved
0.7255	Intermediate Similarity	NPD4308	Phase 3
0.7251	Intermediate Similarity	NPD6797	Phase 2
0.7248	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD9269	Phase 2
0.7241	Intermediate Similarity	NPD9717	Approved
0.7235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7286	Phase 2
0.7234	Intermediate Similarity	NPD9493	Approved
0.723	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2861	Phase 2
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4287	Approved
0.7211	Intermediate Similarity	NPD2797	Approved
0.7211	Intermediate Similarity	NPD1164	Approved
0.7209	Intermediate Similarity	NPD7251	Discontinued
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.7203	Intermediate Similarity	NPD9268	Approved
0.72	Intermediate Similarity	NPD2313	Discontinued
0.7195	Intermediate Similarity	NPD2296	Approved
0.7195	Intermediate Similarity	NPD5977	Approved
0.7195	Intermediate Similarity	NPD5978	Approved
0.7192	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5403	Approved
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD447	Suspended
0.717	Intermediate Similarity	NPD5401	Approved
0.7168	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7808	Phase 3
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5760	Phase 2
0.7134	Intermediate Similarity	NPD3892	Phase 2
0.7134	Intermediate Similarity	NPD5761	Phase 2
0.711	Intermediate Similarity	NPD7685	Pre-registration
0.7107	Intermediate Similarity	NPD4357	Discontinued
0.7101	Intermediate Similarity	NPD5242	Approved
0.7095	Intermediate Similarity	NPD3266	Approved
0.7095	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD411	Approved
0.7086	Intermediate Similarity	NPD1296	Phase 2
0.7076	Intermediate Similarity	NPD7177	Discontinued
0.7075	Intermediate Similarity	NPD4749	Approved
0.7067	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD3225	Approved
0.7022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6971	Discontinued
0.6993	Remote Similarity	NPD4060	Phase 1
0.6993	Remote Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD4307	Phase 2
0.6977	Remote Similarity	NPD7228	Approved
0.6966	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5536	Phase 2
0.6928	Remote Similarity	NPD8032	Phase 2
0.6909	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1729	Discontinued
0.6892	Remote Similarity	NPD1481	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