NPASS Compound

Structure

CID272196 OpenBabel06191716082D 27 30 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 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 0.5000 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 2.5981 -3.5000 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 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 0.0000 -2.0000 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 -2.5981 -0.5000 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 -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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -0.8660 -0.5000 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 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 24 2 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 1 0 0 0 18 22 1 1 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 6 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	394.117
LogP:	4.573
LogD:	3.722
LogS:	-4.782
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	4.297
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.033
MDCK Permeability:	1.9920147678931244e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325
Plasma Protein Binding (PPB):	90.03544616699219%
Volume Distribution (VD):	1.217
Pgp-substrate:	6.677754878997803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.221
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.137
CYP2D6-substrate:	0.451
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.52

ADMET: Excretion

Clearance (CL):	14.519
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.128
Carcinogencity:	0.21
Eye Corrosion:	0.004
Eye Irritation:	0.624
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC272196

Natural Product ID:	NPC272196
*Common Name:**	Phomoarcherin C
IUPAC Name:	(4aR,6aS,12aR,12bS)-11-hydroxy-4,4,6a,9,12b-pentamethyl-3-oxo-2,4a,5,6,12,12a-hexahydro-1H-benzo[a]xanthene-8-carbaldehyde
Synonyms:	Phomoarcherin C
Standard InCHIKey:	JDDYDTDIIFQNAG-WKZKVMAPSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-13-10-16(25)14-11-18-22(4)8-7-19(26)21(2,3)17(22)6-9-23(18,5)27-20(14)15(13)12-24/h10,12,17-18,25H,6-9,11H2,1-5H3/t17-,18+,22-,23-/m0/s1
SMILES:	O=Cc1c(C)cc(c2c1O[C@@]1(C)CC[C@@H]3[C@]([C@H]1C2)(C)CCC(=O)C3(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773757
PubChem CID:	52952105
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001828] Isoflavanols

*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
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21341709]
NPO16660	Phomopsis archeri	Species	Valsaceae	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	5

Activity Type	# Activity
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.9	ug.mL-1	PMID[480183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18.0	ug.mL-1	PMID[480183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15.4	ug.mL-1	PMID[480183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18.8	ug.mL-1	PMID[480183]

☑ 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 NPC272196 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	413
0.1-0.2	1628
0.2-0.3	3231
0.3-0.4	7595
0.4-0.5	10747
0.5-0.6	4698
0.6-0.7	5549
0.7-0.8	6704
0.8-0.85	1845
0.85-0.9	255
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9427	High Similarity	NPC125465
0.9416	High Similarity	NPC472617
0.9404	High Similarity	NPC149526
0.9404	High Similarity	NPC478148
0.9404	High Similarity	NPC474417
0.9355	High Similarity	NPC472618
0.9342	High Similarity	NPC87708
0.9299	High Similarity	NPC100849
0.9286	High Similarity	NPC4547
0.9281	High Similarity	NPC329844
0.9276	High Similarity	NPC232645
0.9276	High Similarity	NPC305965
0.9276	High Similarity	NPC72958
0.9262	High Similarity	NPC470674
0.9262	High Similarity	NPC117716
0.9262	High Similarity	NPC470673
0.9216	High Similarity	NPC40356
0.9216	High Similarity	NPC154683
0.92	High Similarity	NPC470676
0.92	High Similarity	NPC473135
0.92	High Similarity	NPC473132
0.9156	High Similarity	NPC169990
0.9156	High Similarity	NPC210942
0.9156	High Similarity	NPC472799
0.915	High Similarity	NPC470675
0.915	High Similarity	NPC473131
0.9145	High Similarity	NPC158338
0.9145	High Similarity	NPC100985
0.9145	High Similarity	NPC97028
0.9145	High Similarity	NPC329933
0.9145	High Similarity	NPC65589
0.9145	High Similarity	NPC97029
0.9145	High Similarity	NPC288036
0.9139	High Similarity	NPC34802
0.9114	High Similarity	NPC473022
0.9085	High Similarity	NPC202595
0.9085	High Similarity	NPC150928
0.9079	High Similarity	NPC7025
0.9079	High Similarity	NPC27221
0.9079	High Similarity	NPC256672
0.9051	High Similarity	NPC18380
0.9051	High Similarity	NPC137232
0.9045	High Similarity	NPC195167
0.902	High Similarity	NPC473016
0.902	High Similarity	NPC471114
0.9013	High Similarity	NPC123202
0.9013	High Similarity	NPC22005
0.9013	High Similarity	NPC10990
0.9013	High Similarity	NPC300988
0.9013	High Similarity	NPC7943
0.9013	High Similarity	NPC245757
0.9013	High Similarity	NPC304351
0.9007	High Similarity	NPC271288
0.9006	High Similarity	NPC472622
0.9	High Similarity	NPC310340
0.8994	High Similarity	NPC15374
0.8987	High Similarity	NPC292863
0.8987	High Similarity	NPC184326
0.8987	High Similarity	NPC470810
0.8981	High Similarity	NPC158542
0.8981	High Similarity	NPC44199
0.8974	High Similarity	NPC89625
0.8974	High Similarity	NPC149618
0.8968	High Similarity	NPC217447
0.8961	High Similarity	NPC472633
0.8961	High Similarity	NPC470568
0.8961	High Similarity	NPC325983
0.8961	High Similarity	NPC158866
0.8961	High Similarity	NPC29777
0.8961	High Similarity	NPC471115
0.8954	High Similarity	NPC35150
0.8954	High Similarity	NPC106328
0.8947	High Similarity	NPC196114
0.8947	High Similarity	NPC290133
0.8947	High Similarity	NPC24136
0.8947	High Similarity	NPC187282
0.8947	High Similarity	NPC477955
0.8944	High Similarity	NPC472621
0.8938	High Similarity	NPC12461
0.8933	High Similarity	NPC96692
0.8924	High Similarity	NPC474373
0.8924	High Similarity	NPC186113
0.8924	High Similarity	NPC85121
0.891	High Similarity	NPC214632
0.891	High Similarity	NPC280530
0.891	High Similarity	NPC95842
0.891	High Similarity	NPC178964
0.891	High Similarity	NPC135522
0.891	High Similarity	NPC208806
0.8903	High Similarity	NPC178484
0.8903	High Similarity	NPC470569
0.8896	High Similarity	NPC291049
0.8896	High Similarity	NPC10027
0.8896	High Similarity	NPC65775
0.8896	High Similarity	NPC233267
0.8896	High Similarity	NPC474052
0.8896	High Similarity	NPC473978
0.8889	High Similarity	NPC118027
0.8889	High Similarity	NPC296998
0.8889	High Similarity	NPC289042
0.8889	High Similarity	NPC225419
0.8889	High Similarity	NPC56433
0.8889	High Similarity	NPC245584
0.8889	High Similarity	NPC473077
0.8889	High Similarity	NPC190648
0.8889	High Similarity	NPC312929
0.8889	High Similarity	NPC126767
0.8889	High Similarity	NPC308200
0.8882	High Similarity	NPC316262
0.8882	High Similarity	NPC131568
0.8882	High Similarity	NPC131579
0.8882	High Similarity	NPC314653
0.8875	High Similarity	NPC206605
0.8875	High Similarity	NPC473961
0.8875	High Similarity	NPC475106
0.8874	High Similarity	NPC84266
0.8868	High Similarity	NPC186325
0.8868	High Similarity	NPC476280
0.8868	High Similarity	NPC297212
0.8867	High Similarity	NPC469818
0.8867	High Similarity	NPC477272
0.8867	High Similarity	NPC275734
0.8861	High Similarity	NPC282390
0.8861	High Similarity	NPC196448
0.8861	High Similarity	NPC281137
0.8861	High Similarity	NPC201127
0.8859	High Similarity	NPC470671
0.8859	High Similarity	NPC474504
0.8859	High Similarity	NPC470672
0.8859	High Similarity	NPC474487
0.8846	High Similarity	NPC142527
0.8846	High Similarity	NPC470338
0.8846	High Similarity	NPC268992
0.8846	High Similarity	NPC470337
0.8846	High Similarity	NPC273483
0.8846	High Similarity	NPC51824
0.8846	High Similarity	NPC113608
0.8839	High Similarity	NPC227122
0.8839	High Similarity	NPC188403
0.8839	High Similarity	NPC255641
0.8839	High Similarity	NPC147735
0.8839	High Similarity	NPC290954
0.8834	High Similarity	NPC472619
0.8831	High Similarity	NPC145467
0.8831	High Similarity	NPC105415
0.8831	High Similarity	NPC37139
0.8831	High Similarity	NPC39195
0.8827	High Similarity	NPC43319
0.8827	High Similarity	NPC272502
0.8824	High Similarity	NPC82534
0.8824	High Similarity	NPC109183
0.8824	High Similarity	NPC54577
0.8824	High Similarity	NPC195621
0.8824	High Similarity	NPC475052
0.8824	High Similarity	NPC267375
0.8824	High Similarity	NPC214774
0.8824	High Similarity	NPC473078
0.8824	High Similarity	NPC470647
0.8824	High Similarity	NPC301276
0.8824	High Similarity	NPC470132
0.8824	High Similarity	NPC127059
0.8824	High Similarity	NPC312973
0.8824	High Similarity	NPC470131
0.8824	High Similarity	NPC20488
0.8824	High Similarity	NPC67805
0.8824	High Similarity	NPC142405
0.8824	High Similarity	NPC176229
0.8824	High Similarity	NPC88964
0.8824	High Similarity	NPC285630
0.8824	High Similarity	NPC111786
0.8824	High Similarity	NPC470134
0.8824	High Similarity	NPC246948
0.8824	High Similarity	NPC83357
0.8824	High Similarity	NPC470133
0.882	High Similarity	NPC290160
0.882	High Similarity	NPC476295
0.8816	High Similarity	NPC166138
0.8816	High Similarity	NPC5990
0.8816	High Similarity	NPC316816
0.8816	High Similarity	NPC214166
0.8816	High Similarity	NPC11700
0.8816	High Similarity	NPC85162
0.8816	High Similarity	NPC125894
0.8816	High Similarity	NPC478086
0.8816	High Similarity	NPC278249
0.8816	High Similarity	NPC18585
0.8816	High Similarity	NPC106985
0.8816	High Similarity	NPC77794
0.8816	High Similarity	NPC107177
0.8816	High Similarity	NPC223812
0.8816	High Similarity	NPC81697
0.8816	High Similarity	NPC219915
0.8816	High Similarity	NPC189650
0.8812	High Similarity	NPC189552
0.8812	High Similarity	NPC472906
0.8812	High Similarity	NPC273467
0.8808	High Similarity	NPC166689
0.8808	High Similarity	NPC156190
0.8808	High Similarity	NPC17170
0.8808	High Similarity	NPC96408

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 NPC272196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	967
0.2-0.3	1636
0.3-0.4	2615
0.4-0.5	2041
0.5-0.6	936
0.6-0.7	420
0.7-0.8	145
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
0.8931	High Similarity	NPD6959	Discontinued
0.8734	High Similarity	NPD8443	Clinical (unspecified phase)
0.8671	High Similarity	NPD7819	Suspended
0.86	High Similarity	NPD6100	Approved
0.86	High Similarity	NPD6099	Approved
0.8553	High Similarity	NPD2393	Clinical (unspecified phase)
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8516	High Similarity	NPD4378	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2534	Approved
0.8397	Intermediate Similarity	NPD2532	Approved
0.8397	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8366	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8261	Intermediate Similarity	NPD1934	Approved
0.8258	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4380	Phase 2
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD6232	Discontinued
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8171	Intermediate Similarity	NPD3749	Approved
0.817	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1510	Phase 2
0.8166	Intermediate Similarity	NPD5844	Phase 1
0.8158	Intermediate Similarity	NPD1607	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8117	Intermediate Similarity	NPD2796	Approved
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8101	Intermediate Similarity	NPD7390	Discontinued
0.8098	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6166	Phase 2
0.8095	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5494	Approved
0.8039	Intermediate Similarity	NPD6651	Approved
0.8026	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7988	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD1511	Approved
0.7963	Intermediate Similarity	NPD3226	Approved
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3882	Suspended
0.7888	Intermediate Similarity	NPD1512	Approved
0.787	Intermediate Similarity	NPD5711	Approved
0.787	Intermediate Similarity	NPD5710	Approved
0.7853	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7829	Intermediate Similarity	NPD4625	Phase 3
0.7818	Intermediate Similarity	NPD6801	Discontinued
0.7803	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD6799	Approved
0.7763	Intermediate Similarity	NPD4908	Phase 1
0.7746	Intermediate Similarity	NPD7054	Approved
0.7725	Intermediate Similarity	NPD3817	Phase 2
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3748	Approved
0.7701	Intermediate Similarity	NPD7472	Approved
0.7688	Intermediate Similarity	NPD7003	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4749	Approved
0.7665	Intermediate Similarity	NPD5760	Phase 2
0.7665	Intermediate Similarity	NPD5761	Phase 2
0.7658	Intermediate Similarity	NPD2935	Discontinued
0.7657	Intermediate Similarity	NPD6797	Phase 2
0.7636	Intermediate Similarity	NPD7458	Discontinued
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7614	Intermediate Similarity	NPD7251	Discontinued
0.7607	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3818	Discontinued
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.7561	Intermediate Similarity	NPD6273	Approved
0.756	Intermediate Similarity	NPD1465	Phase 2
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5406	Approved
0.7547	Intermediate Similarity	NPD5405	Approved
0.7547	Intermediate Similarity	NPD5404	Approved
0.7547	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD919	Approved
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7457	Intermediate Similarity	NPD7229	Phase 3
0.7446	Intermediate Similarity	NPD4360	Phase 2
0.7446	Intermediate Similarity	NPD4363	Phase 3
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7417	Intermediate Similarity	NPD1201	Approved
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7412	Intermediate Similarity	NPD5402	Approved
0.741	Intermediate Similarity	NPD5403	Approved
0.7405	Intermediate Similarity	NPD5124	Phase 1
0.7405	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7403	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD1247	Approved
0.7391	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD7177	Discontinued
0.7386	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1470	Approved
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7698	Approved
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7299	Intermediate Similarity	NPD7199	Phase 2
0.7294	Intermediate Similarity	NPD37	Approved
0.7289	Intermediate Similarity	NPD5401	Approved
0.7283	Intermediate Similarity	NPD6234	Discontinued
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7255	Intermediate Similarity	NPD3972	Approved
0.7233	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7228	Intermediate Similarity	NPD4287	Approved
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7215	Intermediate Similarity	NPD2313	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD2309	Approved
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.717	Intermediate Similarity	NPD8032	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7161	Intermediate Similarity	NPD1283	Approved
0.7161	Intermediate Similarity	NPD6696	Suspended
0.716	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD1203	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.711	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7105	Intermediate Similarity	NPD1651	Approved
0.7101	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7086	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD230	Phase 1
0.7073	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD3019	Approved
0.7059	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7039	Intermediate Similarity	NPD1548	Phase 1
0.7037	Intermediate Similarity	NPD4097	Suspended

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