NPASS Compound

Structure

NPC469818 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 2.5066 -2.4120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3421 -0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3421 1.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8132 0.3230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1424 0.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1075 -0.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3251 1.7298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3807 0.9882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5066 -1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5066 1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7106 2.1488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8355 1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6710 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6710 -0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5066 0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6710 1.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1260 1.2592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 0.4824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8355 -1.4472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3421 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9339 1.1617 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 7 8 1 0 0 0 0 8 21 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 9 1 1 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 7 1 6 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 21 6 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	362.161
LogP:	6.276
LogD:	4.189
LogS:	-3.229
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	5.011
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.625
MDCK Permeability:	2.2153570171212777e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	99.81231689453125%
Volume Distribution (VD):	1.333
Pgp-substrate:	3.0155913829803467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.294
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.178
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	1.785
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.841
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.559
Skin Sensitization:	0.575
Carcinogencity:	0.232
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.713

Download Data

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

Natural Product: NPC469818

Natural Product ID:	NPC469818
*Common Name:**	Petiolin K
IUPAC Name:	n.a.
Synonyms:	Petiolin K
Standard InCHIKey:	IJCVBOXHKXCRKI-ZNLKAECVSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-10(2)16(22)15-17(23)11(3)18-14-12-9-21(6,25-19(14)15)8-7-13(12)20(4,5)24-18/h10,12-13,23H,7-9H2,1-6H3/t12-,13-,21+/m1/s1
SMILES:	CC(C(=O)c1c2O[C@@]3(C)CC[C@@H]4[C@H](c2c(c(c1O)C)OC4(C)C)C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1209689
PubChem CID:	49862649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18430575]
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20598881]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[536923]
NPT91	Cell Line	KB	Homo sapiens	MIC	>	10.0	ug.mL-1	PMID[536923]

☑ 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 NPC469818 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	391
0.1-0.2	1700
0.2-0.3	3725
0.3-0.4	9287
0.4-0.5	9946
0.5-0.6	4523
0.6-0.7	6211
0.7-0.8	4959
0.8-0.85	1568
0.85-0.9	376
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC473132
0.964	High Similarity	NPC473135
0.964	High Similarity	NPC470676
0.9291	High Similarity	NPC470673
0.9291	High Similarity	NPC470674
0.9291	High Similarity	NPC117716
0.9161	High Similarity	NPC304351
0.9161	High Similarity	NPC245757
0.913	High Similarity	NPC470982
0.913	High Similarity	NPC470983
0.9041	High Similarity	NPC305965
0.9034	High Similarity	NPC473016
0.9007	High Similarity	NPC477272
0.9	High Similarity	NPC470671
0.9	High Similarity	NPC474487
0.9	High Similarity	NPC474504
0.9	High Similarity	NPC470672
0.8958	High Similarity	NPC477955
0.8951	High Similarity	NPC219915
0.8944	High Similarity	NPC157497
0.8944	High Similarity	NPC81337
0.8944	High Similarity	NPC285659
0.8936	High Similarity	NPC240305
0.8912	High Similarity	NPC473131
0.8912	High Similarity	NPC470675
0.8889	High Similarity	NPC271288
0.8881	High Similarity	NPC144499
0.8867	High Similarity	NPC272196
0.8865	High Similarity	NPC248995
0.8865	High Similarity	NPC272844
0.8865	High Similarity	NPC254168
0.8851	High Similarity	NPC87708
0.8844	High Similarity	NPC150928
0.8844	High Similarity	NPC471115
0.8844	High Similarity	NPC29777
0.8828	High Similarity	NPC82534
0.8819	High Similarity	NPC166138
0.8819	High Similarity	NPC5990
0.8819	High Similarity	NPC38219
0.8819	High Similarity	NPC106985
0.8819	High Similarity	NPC18585
0.8819	High Similarity	NPC112749
0.8808	High Similarity	NPC472617
0.8803	High Similarity	NPC472343
0.88	High Similarity	NPC4547
0.8792	High Similarity	NPC329844
0.8792	High Similarity	NPC95842
0.8792	High Similarity	NPC280530
0.8792	High Similarity	NPC178964
0.8786	High Similarity	NPC101752
0.8784	High Similarity	NPC72958
0.8784	High Similarity	NPC478148
0.8784	High Similarity	NPC474417
0.8784	High Similarity	NPC149526
0.8784	High Similarity	NPC209142
0.8784	High Similarity	NPC312549
0.8784	High Similarity	NPC476162
0.8784	High Similarity	NPC232645
0.8776	High Similarity	NPC473978
0.8776	High Similarity	NPC100985
0.8776	High Similarity	NPC65775
0.8776	High Similarity	NPC97029
0.8776	High Similarity	NPC158338
0.8776	High Similarity	NPC97028
0.8776	High Similarity	NPC10027
0.8776	High Similarity	NPC288036
0.8776	High Similarity	NPC65589
0.8767	High Similarity	NPC474108
0.8767	High Similarity	NPC473077
0.8767	High Similarity	NPC140120
0.8767	High Similarity	NPC296998
0.8767	High Similarity	NPC308200
0.8767	High Similarity	NPC177995
0.8759	High Similarity	NPC131568
0.8759	High Similarity	NPC206212
0.8759	High Similarity	NPC186628
0.8759	High Similarity	NPC131579
0.8759	High Similarity	NPC71184
0.8758	High Similarity	NPC473022
0.875	High Similarity	NPC470636
0.875	High Similarity	NPC293852
0.875	High Similarity	NPC217083
0.875	High Similarity	NPC78803
0.875	High Similarity	NPC96791
0.875	High Similarity	NPC310340
0.875	High Similarity	NPC299080
0.875	High Similarity	NPC59739
0.875	High Similarity	NPC62840
0.875	High Similarity	NPC214236
0.875	High Similarity	NPC472618
0.875	High Similarity	NPC226942
0.8741	High Similarity	NPC69769
0.8741	High Similarity	NPC275734
0.8733	High Similarity	NPC275575
0.8733	High Similarity	NPC166054
0.8733	High Similarity	NPC55662
0.8732	High Similarity	NPC470669
0.8732	High Similarity	NPC131130
0.8732	High Similarity	NPC199458
0.8732	High Similarity	NPC180501
0.8732	High Similarity	NPC470668
0.8732	High Similarity	NPC183639
0.8732	High Similarity	NPC268178
0.8732	High Similarity	NPC54820
0.8725	High Similarity	NPC142527
0.8725	High Similarity	NPC217447
0.8716	High Similarity	NPC472633
0.8716	High Similarity	NPC227122
0.8716	High Similarity	NPC158866
0.8707	High Similarity	NPC208303
0.8707	High Similarity	NPC27221
0.8707	High Similarity	NPC256672
0.8707	High Similarity	NPC296869
0.8707	High Similarity	NPC161864
0.8707	High Similarity	NPC39195
0.8707	High Similarity	NPC7025
0.8707	High Similarity	NPC145467
0.8699	High Similarity	NPC470647
0.8699	High Similarity	NPC142405
0.8699	High Similarity	NPC312973
0.8699	High Similarity	NPC301276
0.8699	High Similarity	NPC195621
0.8699	High Similarity	NPC176229
0.8699	High Similarity	NPC187282
0.8699	High Similarity	NPC290133
0.8699	High Similarity	NPC246948
0.8699	High Similarity	NPC285630
0.8699	High Similarity	NPC475052
0.8699	High Similarity	NPC220418
0.8699	High Similarity	NPC20488
0.8699	High Similarity	NPC127059
0.8699	High Similarity	NPC196114
0.8699	High Similarity	NPC88964
0.8699	High Similarity	NPC267375
0.8699	High Similarity	NPC54577
0.8699	High Similarity	NPC67805
0.8699	High Similarity	NPC24136
0.8699	High Similarity	NPC214774
0.8699	High Similarity	NPC111786
0.8699	High Similarity	NPC83357
0.8696	High Similarity	NPC279566
0.869	High Similarity	NPC172182
0.869	High Similarity	NPC223812
0.869	High Similarity	NPC81697
0.869	High Similarity	NPC125894
0.869	High Similarity	NPC262935
0.869	High Similarity	NPC11700
0.869	High Similarity	NPC278249
0.869	High Similarity	NPC18886
0.869	High Similarity	NPC214166
0.869	High Similarity	NPC316816
0.869	High Similarity	NPC77794
0.869	High Similarity	NPC478086
0.869	High Similarity	NPC85162
0.869	High Similarity	NPC251182
0.869	High Similarity	NPC107177
0.8684	High Similarity	NPC474373
0.8681	High Similarity	NPC147688
0.8681	High Similarity	NPC205006
0.8681	High Similarity	NPC111201
0.8681	High Similarity	NPC156190
0.8681	High Similarity	NPC96408
0.8681	High Similarity	NPC279650
0.8681	High Similarity	NPC40118
0.8681	High Similarity	NPC232021
0.8681	High Similarity	NPC258630
0.8681	High Similarity	NPC17170
0.8681	High Similarity	NPC248372
0.8681	High Similarity	NPC64908
0.8681	High Similarity	NPC126534
0.8681	High Similarity	NPC156590
0.8681	High Similarity	NPC118840
0.8681	High Similarity	NPC110038
0.8681	High Similarity	NPC470555
0.8681	High Similarity	NPC282300
0.8681	High Similarity	NPC166689
0.8675	High Similarity	NPC164427
0.8671	High Similarity	NPC96565
0.8671	High Similarity	NPC55018
0.8671	High Similarity	NPC270913
0.8671	High Similarity	NPC53181
0.8671	High Similarity	NPC19476
0.8671	High Similarity	NPC220062
0.8671	High Similarity	NPC301217
0.8671	High Similarity	NPC303633
0.8671	High Similarity	NPC241975
0.8671	High Similarity	NPC216978
0.8671	High Similarity	NPC217186
0.8667	High Similarity	NPC472799
0.8667	High Similarity	NPC169990
0.8667	High Similarity	NPC210942
0.8662	High Similarity	NPC474624
0.8662	High Similarity	NPC322301
0.8662	High Similarity	NPC255801
0.8662	High Similarity	NPC131782
0.8662	High Similarity	NPC138047
0.8658	High Similarity	NPC178484
0.8658	High Similarity	NPC474021
0.8658	High Similarity	NPC477672
0.8658	High Similarity	NPC474023

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 NPC469818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	1065
0.2-0.3	1862
0.3-0.4	2650
0.4-0.5	1911
0.5-0.6	901
0.6-0.7	298
0.7-0.8	94
0.8-0.85	16
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.863	High Similarity	NPD7410	Clinical (unspecified phase)
0.8571	High Similarity	NPD6959	Discontinued
0.8542	High Similarity	NPD2800	Approved
0.8511	High Similarity	NPD6651	Approved
0.8503	High Similarity	NPD4378	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD7819	Suspended
0.8301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.8219	Intermediate Similarity	NPD1549	Phase 2
0.8207	Intermediate Similarity	NPD6100	Approved
0.8207	Intermediate Similarity	NPD6099	Approved
0.817	Intermediate Similarity	NPD7411	Suspended
0.8105	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD7075	Discontinued
0.8014	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7986	Intermediate Similarity	NPD1240	Approved
0.7959	Intermediate Similarity	NPD2796	Approved
0.795	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1511	Approved
0.7925	Intermediate Similarity	NPD5494	Approved
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7768	Phase 2
0.7843	Intermediate Similarity	NPD1512	Approved
0.784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6166	Phase 2
0.7834	Intermediate Similarity	NPD2801	Approved
0.7805	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.777	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6232	Discontinued
0.7716	Intermediate Similarity	NPD5711	Approved
0.7716	Intermediate Similarity	NPD5710	Approved
0.7712	Intermediate Similarity	NPD7390	Discontinued
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD7074	Phase 3
0.7643	Intermediate Similarity	NPD6599	Discontinued
0.7625	Intermediate Similarity	NPD3882	Suspended
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7603	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6799	Approved
0.759	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD5844	Phase 1
0.758	Intermediate Similarity	NPD3226	Approved
0.7568	Intermediate Similarity	NPD5124	Phase 1
0.7568	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1243	Approved
0.7545	Intermediate Similarity	NPD7472	Approved
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7466	Intermediate Similarity	NPD4908	Phase 1
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7453	Intermediate Similarity	NPD3817	Phase 2
0.7434	Intermediate Similarity	NPD2344	Approved
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.7365	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD920	Approved
0.7321	Intermediate Similarity	NPD3818	Discontinued
0.7294	Intermediate Similarity	NPD5953	Discontinued
0.7288	Intermediate Similarity	NPD4363	Phase 3
0.7288	Intermediate Similarity	NPD4360	Phase 2
0.7278	Intermediate Similarity	NPD7286	Phase 2
0.7255	Intermediate Similarity	NPD5406	Approved
0.7255	Intermediate Similarity	NPD5404	Approved
0.7255	Intermediate Similarity	NPD5405	Approved
0.7255	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3268	Approved
0.7244	Intermediate Similarity	NPD2309	Approved
0.7233	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD1610	Phase 2
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2798	Approved
0.7209	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7163	Intermediate Similarity	NPD7340	Approved
0.7159	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7134	Intermediate Similarity	NPD5402	Approved
0.7107	Intermediate Similarity	NPD5401	Approved
0.7107	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1201	Approved
0.7078	Intermediate Similarity	NPD4308	Phase 3
0.7071	Intermediate Similarity	NPD1398	Phase 1
0.707	Intermediate Similarity	NPD7003	Approved
0.7056	Intermediate Similarity	NPD4361	Phase 2
0.7056	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD9717	Approved
0.7055	Intermediate Similarity	NPD1608	Approved
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.703	Intermediate Similarity	NPD4288	Approved
0.7027	Intermediate Similarity	NPD1470	Approved
0.7006	Intermediate Similarity	NPD919	Approved
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD2403	Approved
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1471	Phase 3
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD422	Phase 1
0.6982	Remote Similarity	NPD7229	Phase 3
0.697	Remote Similarity	NPD5760	Phase 2
0.697	Remote Similarity	NPD5761	Phase 2
0.6968	Remote Similarity	NPD7033	Discontinued
0.6951	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1247	Approved
0.6919	Remote Similarity	NPD3751	Discontinued
0.6913	Remote Similarity	NPD3267	Approved
0.6913	Remote Similarity	NPD3266	Approved
0.6908	Remote Similarity	NPD411	Approved
0.6908	Remote Similarity	NPD3764	Approved
0.6905	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6782	Approved
0.6902	Remote Similarity	NPD6778	Approved
0.6902	Remote Similarity	NPD6780	Approved
0.6902	Remote Similarity	NPD6777	Approved
0.6902	Remote Similarity	NPD6779	Approved
0.6902	Remote Similarity	NPD6776	Approved
0.6894	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6585	Discontinued
0.6887	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6832	Phase 2
0.6882	Remote Similarity	NPD7697	Approved
0.6882	Remote Similarity	NPD7696	Phase 3
0.6882	Remote Similarity	NPD7698	Approved
0.6882	Remote Similarity	NPD3787	Discontinued
0.6878	Remote Similarity	NPD8151	Discontinued
0.6859	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8434	Phase 2
0.6854	Remote Similarity	NPD8150	Discontinued
0.6852	Remote Similarity	NPD6273	Approved
0.6849	Remote Similarity	NPD17	Approved
0.6846	Remote Similarity	NPD3225	Approved
0.6839	Remote Similarity	NPD1729	Discontinued
0.6831	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1548	Phase 1
0.6824	Remote Similarity	NPD3972	Approved
0.6824	Remote Similarity	NPD7199	Phase 2
0.6821	Remote Similarity	NPD7177	Discontinued
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD4307	Phase 2
0.681	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD37	Approved
0.6806	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7783	Phase 2
0.6805	Remote Similarity	NPD6234	Discontinued
0.6798	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7435	Discontinued
0.6786	Remote Similarity	NPD4967	Phase 2
0.6786	Remote Similarity	NPD4965	Approved
0.6786	Remote Similarity	NPD4966	Approved
0.6781	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD447	Suspended
0.6774	Remote Similarity	NPD230	Phase 1
0.6772	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7584	Approved
0.677	Remote Similarity	NPD3300	Phase 2
0.6761	Remote Similarity	NPD6104	Discontinued
0.6759	Remote Similarity	NPD7644	Approved
0.6755	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7871	Phase 2
0.6755	Remote Similarity	NPD7870	Phase 2
0.6747	Remote Similarity	NPD5889	Approved
0.6747	Remote Similarity	NPD5890	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data