NPASS Compound

Structure

NPC210942 OpenBabel07101718322D 32 34 0 0 0 0 0 0 0 0999 V2000 6.0622 -4.5000 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 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 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 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 1.7321 -5.0000 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 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 3.4641 -2.0000 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 0.8660 -0.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 27 1 0 0 0 0 13 31 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 17 22 1 0 0 0 0 17 28 2 0 0 0 0 18 20 1 0 0 0 0 18 26 2 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 31 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 32 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.22
Volume:	470.102
LogP:	7.715
LogD:	4.912
LogS:	-2.811
# Rotatable Bonds:	6
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	3.405
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	1.6500853234902024e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.267
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	87.9038314819336%
Volume Distribution (VD):	2.472
Pgp-substrate:	11.30399227142334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.521
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.838
CYP2C19-substrate:	0.142
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	6.36
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.384
Carcinogencity:	0.712
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC210942

Natural Product ID:	NPC210942
*Common Name:**	Adenaflorine C
IUPAC Name:	1-[6,7-dihydroxy-3,3-dimethyl-9-(3-methylbut-2-enoxy)-8-(3-methylbut-2-enyl)benzo[f]chromen-5-yl]ethanone
Synonyms:	Adenaflorine C
Standard InCHIKey:	ILDBGZHKNVSTSA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H32O5/c1-15(2)8-9-19-21(31-13-11-16(3)4)14-20-18-10-12-27(6,7)32-26(18)22(17(5)28)25(30)23(20)24(19)29/h8,10-12,14,29-30H,9,13H2,1-7H3
SMILES:	CC(=CCOc1cc2c3C=CC(Oc3c(c(c2c(c1CC=C(C)C)O)O)C(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463700
PubChem CID:	10478186
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO17605	Adenaria floribunda	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043429]
NPO17605	Adenaria floribunda	Species	Lythraceae	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	1.2	ug.mL-1	PMID[496870]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.1	ug.mL-1	PMID[496870]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	1.4	ug.mL-1	PMID[496870]

☑ 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 NPC210942 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	401
0.1-0.2	1583
0.2-0.3	3514
0.3-0.4	9024
0.4-0.5	9579
0.5-0.6	3435
0.6-0.7	5386
0.7-0.8	5526
0.8-0.85	2432
0.85-0.9	1464
0.9-0.95	340
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169990
0.973	High Similarity	NPC329844
0.9728	High Similarity	NPC478148
0.9728	High Similarity	NPC474417
0.9728	High Similarity	NPC149526
0.9726	High Similarity	NPC97029
0.9726	High Similarity	NPC100985
0.9726	High Similarity	NPC158338
0.9726	High Similarity	NPC288036
0.9726	High Similarity	NPC65589
0.9726	High Similarity	NPC97028
0.9658	High Similarity	NPC7025
0.9658	High Similarity	NPC256672
0.9658	High Similarity	NPC27221
0.9595	High Similarity	NPC232645
0.9595	High Similarity	NPC72958
0.9589	High Similarity	NPC7943
0.9589	High Similarity	NPC123202
0.9589	High Similarity	NPC22005
0.953	High Similarity	NPC87708
0.9463	High Similarity	NPC258249
0.9459	High Similarity	NPC10027
0.9459	High Similarity	NPC65775
0.9459	High Similarity	NPC329933
0.9456	High Similarity	NPC34802
0.94	High Similarity	NPC40356
0.94	High Similarity	NPC154683
0.9384	High Similarity	NPC189650
0.9338	High Similarity	NPC193200
0.9329	High Similarity	NPC474052
0.9329	High Similarity	NPC269420
0.9315	High Similarity	NPC84266
0.9281	High Similarity	NPC281137
0.9281	High Similarity	NPC282390
0.9281	High Similarity	NPC44199
0.9272	High Similarity	NPC45934
0.9272	High Similarity	NPC217447
0.9272	High Similarity	NPC142527
0.9267	High Similarity	NPC472633
0.9267	High Similarity	NPC158866
0.9267	High Similarity	NPC325983
0.9267	High Similarity	NPC202595
0.9262	High Similarity	NPC37139
0.9257	High Similarity	NPC196114
0.9247	High Similarity	NPC94076
0.9247	High Similarity	NPC182255
0.9221	High Similarity	NPC474373
0.9211	High Similarity	NPC95842
0.9211	High Similarity	NPC472799
0.9211	High Similarity	NPC135522
0.9211	High Similarity	NPC178964
0.9211	High Similarity	NPC280530
0.92	High Similarity	NPC233267
0.92	High Similarity	NPC291049
0.9195	High Similarity	NPC97716
0.9195	High Similarity	NPC24673
0.9195	High Similarity	NPC125801
0.9195	High Similarity	NPC201731
0.9195	High Similarity	NPC104406
0.9195	High Similarity	NPC79469
0.9195	High Similarity	NPC473077
0.9195	High Similarity	NPC237635
0.9195	High Similarity	NPC296998
0.9195	High Similarity	NPC283234
0.9189	High Similarity	NPC311741
0.9189	High Similarity	NPC234629
0.9189	High Similarity	NPC271288
0.9184	High Similarity	NPC310340
0.9184	High Similarity	NPC226636
0.9184	High Similarity	NPC11561
0.9178	High Similarity	NPC159275
0.9178	High Similarity	NPC150522
0.9178	High Similarity	NPC471587
0.9178	High Similarity	NPC241100
0.9177	High Similarity	NPC218226
0.9172	High Similarity	NPC303174
0.9161	High Similarity	NPC470810
0.9161	High Similarity	NPC186325
0.9156	High Similarity	NPC96342
0.9156	High Similarity	NPC272196
0.9156	High Similarity	NPC246647
0.9156	High Similarity	NPC164110
0.9156	High Similarity	NPC212967
0.9156	High Similarity	NPC268360
0.915	High Similarity	NPC275575
0.9145	High Similarity	NPC273483
0.9139	High Similarity	NPC227122
0.9139	High Similarity	NPC470568
0.9139	High Similarity	NPC255641
0.9139	High Similarity	NPC188403
0.9139	High Similarity	NPC29777
0.9139	High Similarity	NPC37348
0.9139	High Similarity	NPC471115
0.9139	High Similarity	NPC290954
0.9133	High Similarity	NPC132592
0.9133	High Similarity	NPC6511
0.9133	High Similarity	NPC160821
0.9133	High Similarity	NPC145467
0.9133	High Similarity	NPC266572
0.9133	High Similarity	NPC105415
0.9128	High Similarity	NPC301276
0.9128	High Similarity	NPC214774
0.9128	High Similarity	NPC163846
0.9128	High Similarity	NPC290133
0.9128	High Similarity	NPC187282
0.9128	High Similarity	NPC24136
0.9128	High Similarity	NPC20488
0.9128	High Similarity	NPC312973
0.9128	High Similarity	NPC83357
0.9128	High Similarity	NPC475052
0.9128	High Similarity	NPC130176
0.9128	High Similarity	NPC285630
0.9128	High Similarity	NPC124729
0.9128	High Similarity	NPC267375
0.9128	High Similarity	NPC54577
0.9128	High Similarity	NPC246948
0.9128	High Similarity	NPC99454
0.9128	High Similarity	NPC142405
0.9128	High Similarity	NPC225173
0.9128	High Similarity	NPC470647
0.9128	High Similarity	NPC127059
0.9128	High Similarity	NPC195621
0.9128	High Similarity	NPC67805
0.9128	High Similarity	NPC176229
0.9128	High Similarity	NPC477955
0.9128	High Similarity	NPC88964
0.9128	High Similarity	NPC111786
0.9122	High Similarity	NPC166138
0.9122	High Similarity	NPC18585
0.9122	High Similarity	NPC214166
0.9122	High Similarity	NPC478086
0.9122	High Similarity	NPC106985
0.9122	High Similarity	NPC185276
0.9122	High Similarity	NPC316816
0.9122	High Similarity	NPC11700
0.9122	High Similarity	NPC219915
0.9116	High Similarity	NPC147688
0.9116	High Similarity	NPC156590
0.9116	High Similarity	NPC64908
0.9116	High Similarity	NPC282300
0.9116	High Similarity	NPC118840
0.9116	High Similarity	NPC110969
0.9116	High Similarity	NPC103362
0.9116	High Similarity	NPC205006
0.9114	High Similarity	NPC272502
0.9114	High Similarity	NPC43319
0.911	High Similarity	NPC78913
0.911	High Similarity	NPC96565
0.911	High Similarity	NPC53181
0.911	High Similarity	NPC301217
0.911	High Similarity	NPC220062
0.911	High Similarity	NPC303633
0.911	High Similarity	NPC18260
0.911	High Similarity	NPC217186
0.911	High Similarity	NPC216978
0.911	High Similarity	NPC55018
0.911	High Similarity	NPC23257
0.9103	High Similarity	NPC189552
0.9103	High Similarity	NPC18380
0.9103	High Similarity	NPC137232
0.9103	High Similarity	NPC273467
0.9103	High Similarity	NPC66288
0.9097	High Similarity	NPC55443
0.9097	High Similarity	NPC18699
0.9097	High Similarity	NPC85121
0.9097	High Similarity	NPC210459
0.9097	High Similarity	NPC177650
0.9097	High Similarity	NPC195167
0.9091	High Similarity	NPC180924
0.9085	High Similarity	NPC93552
0.9085	High Similarity	NPC214632
0.9079	High Similarity	NPC133856
0.9079	High Similarity	NPC470569
0.9073	High Similarity	NPC473016
0.9073	High Similarity	NPC473978
0.9073	High Similarity	NPC5173
0.9067	High Similarity	NPC118027
0.9067	High Similarity	NPC110303
0.9067	High Similarity	NPC126767
0.9067	High Similarity	NPC300988
0.9067	High Similarity	NPC10990
0.9067	High Similarity	NPC56433
0.9067	High Similarity	NPC289042
0.9067	High Similarity	NPC308200
0.9067	High Similarity	NPC71055
0.9067	High Similarity	NPC259632
0.9067	High Similarity	NPC190648
0.9067	High Similarity	NPC23728
0.9067	High Similarity	NPC312929
0.9067	High Similarity	NPC245584
0.906	High Similarity	NPC131579
0.906	High Similarity	NPC236766
0.906	High Similarity	NPC319752
0.906	High Similarity	NPC216538
0.906	High Similarity	NPC235217
0.906	High Similarity	NPC473014
0.906	High Similarity	NPC197252
0.906	High Similarity	NPC273538
0.906	High Similarity	NPC209040
0.906	High Similarity	NPC224714

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 NPC210942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	978
0.2-0.3	1503
0.3-0.4	2547
0.4-0.5	1943
0.5-0.6	1107
0.6-0.7	484
0.7-0.8	174
0.8-0.85	36
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD7819	Suspended
0.906	High Similarity	NPD4378	Clinical (unspecified phase)
0.8981	High Similarity	NPD6959	Discontinued
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8808	High Similarity	NPD7410	Clinical (unspecified phase)
0.8782	High Similarity	NPD8443	Clinical (unspecified phase)
0.8716	High Similarity	NPD1552	Clinical (unspecified phase)
0.8716	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD1510	Phase 2
0.8658	High Similarity	NPD1549	Phase 2
0.8649	High Similarity	NPD2796	Approved
0.8642	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD6232	Discontinued
0.8571	High Similarity	NPD1607	Approved
0.8562	High Similarity	NPD2533	Approved
0.8562	High Similarity	NPD2532	Approved
0.8562	High Similarity	NPD2534	Approved
0.8553	High Similarity	NPD7075	Discontinued
0.8535	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD970	Clinical (unspecified phase)
0.8526	High Similarity	NPD4380	Phase 2
0.8497	Intermediate Similarity	NPD1511	Approved
0.8491	Intermediate Similarity	NPD7768	Phase 2
0.8481	Intermediate Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8435	Intermediate Similarity	NPD1240	Approved
0.8421	Intermediate Similarity	NPD3750	Approved
0.84	Intermediate Similarity	NPD6100	Approved
0.84	Intermediate Similarity	NPD6099	Approved
0.8387	Intermediate Similarity	NPD1512	Approved
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3749	Approved
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8302	Intermediate Similarity	NPD6801	Discontinued
0.8291	Intermediate Similarity	NPD6599	Discontinued
0.8261	Intermediate Similarity	NPD3882	Suspended
0.8258	Intermediate Similarity	NPD7390	Discontinued
0.8231	Intermediate Similarity	NPD4625	Phase 3
0.8228	Intermediate Similarity	NPD3226	Approved
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3817	Phase 2
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8141	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8117	Intermediate Similarity	NPD2800	Approved
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5494	Approved
0.8105	Intermediate Similarity	NPD2346	Discontinued
0.8095	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD3748	Approved
0.8065	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7472	Approved
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8036	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1243	Approved
0.7987	Intermediate Similarity	NPD920	Approved
0.7962	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6651	Approved
0.7953	Intermediate Similarity	NPD7251	Discontinued
0.7907	Intermediate Similarity	NPD7808	Phase 3
0.7904	Intermediate Similarity	NPD5710	Approved
0.7904	Intermediate Similarity	NPD5711	Approved
0.7895	Intermediate Similarity	NPD6797	Phase 2
0.7888	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2344	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7831	Intermediate Similarity	NPD919	Approved
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5404	Approved
0.7806	Intermediate Similarity	NPD5406	Approved
0.7806	Intermediate Similarity	NPD5405	Approved
0.7806	Intermediate Similarity	NPD5408	Approved
0.7798	Intermediate Similarity	NPD7229	Phase 3
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7764	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD5402	Approved
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1247	Approved
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7687	Intermediate Similarity	NPD1201	Approved
0.7682	Intermediate Similarity	NPD4908	Phase 1
0.7673	Intermediate Similarity	NPD2309	Approved
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.765	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5401	Approved
0.7628	Intermediate Similarity	NPD7033	Discontinued
0.7628	Intermediate Similarity	NPD4308	Phase 3
0.7616	Intermediate Similarity	NPD7177	Discontinued
0.761	Intermediate Similarity	NPD7003	Approved
0.7603	Intermediate Similarity	NPD1651	Approved
0.76	Intermediate Similarity	NPD1470	Approved
0.7597	Intermediate Similarity	NPD943	Approved
0.7584	Intermediate Similarity	NPD4749	Approved
0.7582	Intermediate Similarity	NPD3268	Approved
0.7569	Intermediate Similarity	NPD4363	Phase 3
0.7569	Intermediate Similarity	NPD4360	Phase 2
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.755	Intermediate Similarity	NPD2798	Approved
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7533	Intermediate Similarity	NPD1283	Approved
0.7527	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7483	Intermediate Similarity	NPD2797	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD6782	Approved
0.7459	Intermediate Similarity	NPD6777	Approved
0.7459	Intermediate Similarity	NPD6779	Approved
0.7459	Intermediate Similarity	NPD6778	Approved
0.7459	Intermediate Similarity	NPD6776	Approved
0.7459	Intermediate Similarity	NPD6781	Approved
0.7459	Intermediate Similarity	NPD6780	Approved
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4288	Approved
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7783	Phase 2
0.7433	Intermediate Similarity	NPD7435	Discontinued
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7697	Approved
0.743	Intermediate Similarity	NPD8150	Discontinued
0.7427	Intermediate Similarity	NPD7199	Phase 2
0.7423	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1471	Phase 3
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7414	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5761	Phase 2
0.7381	Intermediate Similarity	NPD5760	Phase 2
0.7378	Intermediate Similarity	NPD6273	Approved
0.7372	Intermediate Similarity	NPD2979	Phase 3
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7372	Intermediate Similarity	NPD4307	Phase 2
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3764	Approved
0.7355	Intermediate Similarity	NPD411	Approved
0.7348	Intermediate Similarity	NPD4287	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD1281	Approved
0.7333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD37	Approved
0.732	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4626	Approved
0.731	Intermediate Similarity	NPD6234	Discontinued
0.7296	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7287	Intermediate Similarity	NPD6823	Phase 2
0.7285	Intermediate Similarity	NPD9717	Approved
0.7277	Intermediate Similarity	NPD7701	Phase 2
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3267	Approved
0.7255	Intermediate Similarity	NPD3266	Approved
0.725	Intermediate Similarity	NPD2438	Suspended
0.725	Intermediate Similarity	NPD4477	Approved
0.725	Intermediate Similarity	NPD4476	Approved
0.7248	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1729	Discontinued
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7584	Approved
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data