NPASS Compound

Structure

CID323441 OpenBabel06191716172D 33 36 0 0 1 0 0 0 0 0999 V2000 1.6422 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5598 2.7084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4843 2.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9976 1.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8210 -2.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6430 -1.8961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2832 2.0497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6423 1.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1293 0.0936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2048 -0.1174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8211 1.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6420 -0.9488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8209 -0.4743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4635 1.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6423 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5407 0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8213 -0.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8208 0.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2048 2.0133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4635 0.4738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8210 -1.4226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8211 0.4738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8217 -1.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4889 0.9479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -2.8448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6424 0.0004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6401 -0.0597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8221 -2.3704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5972 1.3955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1293 1.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 6 24 1 0 0 0 0 8 32 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 6 0 0 0 16 24 1 0 0 0 0 17 27 2 0 0 0 0 17 33 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 18 28 2 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 19 29 2 0 0 0 0 20 30 2 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 4 1 6 0 0 0 23 5 1 6 0 0 0 24 26 1 1 0 0 0 25 7 1 1 0 0 0 25 31 1 0 0 0 0 26 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	469.739
LogP:	3.262
LogD:	2.849
LogS:	-4.7
# Rotatable Bonds:	2
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.869
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.39
MDCK Permeability:	2.2270778572419658e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.708
30% Bioavailability (F30%):	0.772

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	63.85438537597656%
Volume Distribution (VD):	0.446
Pgp-substrate:	36.37747573852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	2.356
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.322
Carcinogencity:	0.923
Eye Corrosion:	0.98
Eye Irritation:	0.412
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC323441

Natural Product ID:	NPC323441
*Common Name:**	Berkeleyone B
IUPAC Name:	n.a.
Synonyms:	Berkeleyone B
Standard InCHIKey:	IWYHWTWGKBGNTO-GSISZECUSA-N
Standard InCHI:	InChI=1S/C26H34O7/c1-14-23(5)13-16-22(4)11-10-17(27)33-21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h9,16,31H,1,10-13H2,2-8H3/t16-,22+,23+,24-,25-,26-/m0/s1
SMILES:	COC(=O)[C@@]12C(=O)[C@@](C)(O)C(=O)[C@](C1=C)(C)C[C@@H]1[C@]2(C)CC=C2[C@@]1(C)CCC(=O)OC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911628
PubChem CID:	57398142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones

*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
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	Berkeley Pit Lake, Butte, Montana	n.a.	PMID[18330993]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22295871]
NPO40981	Penicillium chrysogenum MT-12	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28960979]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT277	Individual Protein	Caspase-1	Homo sapiens	Inhibition	=	100.0	%	PMID[546116]
NPT5270	Individual Protein	Interleukin-1 beta	Homo sapiens	IC50	=	3700.0	nM	PMID[546116]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[546117]

☑ 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 NPC323441 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	238
0.1-0.2	1481
0.2-0.3	4896
0.3-0.4	10108
0.4-0.5	12943
0.5-0.6	7281
0.6-0.7	5137
0.7-0.8	603
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC325769
0.8958	High Similarity	NPC269492
0.8936	High Similarity	NPC327515
0.8438	Intermediate Similarity	NPC263977
0.8252	Intermediate Similarity	NPC90177
0.8247	Intermediate Similarity	NPC476369
0.8247	Intermediate Similarity	NPC476437
0.8182	Intermediate Similarity	NPC476415
0.8073	Intermediate Similarity	NPC159333
0.802	Intermediate Similarity	NPC223169
0.7981	Intermediate Similarity	NPC80781
0.7941	Intermediate Similarity	NPC170131
0.79	Intermediate Similarity	NPC271652
0.79	Intermediate Similarity	NPC476416
0.787	Intermediate Similarity	NPC220705
0.7864	Intermediate Similarity	NPC316598
0.785	Intermediate Similarity	NPC475294
0.7822	Intermediate Similarity	NPC148964
0.7818	Intermediate Similarity	NPC193948
0.7818	Intermediate Similarity	NPC147180
0.7812	Intermediate Similarity	NPC156981
0.7788	Intermediate Similarity	NPC46761
0.7778	Intermediate Similarity	NPC474700
0.7778	Intermediate Similarity	NPC322903
0.7767	Intermediate Similarity	NPC285513
0.7767	Intermediate Similarity	NPC254496
0.7757	Intermediate Similarity	NPC32006
0.7757	Intermediate Similarity	NPC1679
0.7757	Intermediate Similarity	NPC292588
0.7757	Intermediate Similarity	NPC85529
0.7755	Intermediate Similarity	NPC476409
0.7755	Intermediate Similarity	NPC231599
0.7755	Intermediate Similarity	NPC171722
0.7745	Intermediate Similarity	NPC777
0.7732	Intermediate Similarity	NPC474680
0.7723	Intermediate Similarity	NPC131840
0.7723	Intermediate Similarity	NPC169343
0.7714	Intermediate Similarity	NPC476888
0.7714	Intermediate Similarity	NPC93744
0.77	Intermediate Similarity	NPC198818
0.77	Intermediate Similarity	NPC113393
0.7699	Intermediate Similarity	NPC239273
0.7685	Intermediate Similarity	NPC473169
0.7684	Intermediate Similarity	NPC14203
0.7684	Intermediate Similarity	NPC229584
0.767	Intermediate Similarity	NPC62516
0.767	Intermediate Similarity	NPC476797
0.767	Intermediate Similarity	NPC157113
0.7664	Intermediate Similarity	NPC284865
0.766	Intermediate Similarity	NPC28319
0.7658	Intermediate Similarity	NPC100267
0.7658	Intermediate Similarity	NPC277769
0.7658	Intermediate Similarity	NPC264634
0.7658	Intermediate Similarity	NPC269530
0.7658	Intermediate Similarity	NPC475524
0.7653	Intermediate Similarity	NPC229717
0.7647	Intermediate Similarity	NPC84893
0.7647	Intermediate Similarity	NPC293086
0.7642	Intermediate Similarity	NPC476890
0.7642	Intermediate Similarity	NPC40918
0.7642	Intermediate Similarity	NPC136289
0.7619	Intermediate Similarity	NPC474802
0.7619	Intermediate Similarity	NPC476933
0.7619	Intermediate Similarity	NPC174314
0.7619	Intermediate Similarity	NPC117685
0.7611	Intermediate Similarity	NPC270478
0.76	Intermediate Similarity	NPC474570
0.76	Intermediate Similarity	NPC284561
0.7596	Intermediate Similarity	NPC38530
0.7596	Intermediate Similarity	NPC224356
0.7596	Intermediate Similarity	NPC175351
0.7596	Intermediate Similarity	NPC121402
0.7596	Intermediate Similarity	NPC132753
0.7596	Intermediate Similarity	NPC76266
0.7596	Intermediate Similarity	NPC151681
0.7596	Intermediate Similarity	NPC84335
0.7589	Intermediate Similarity	NPC472929
0.7573	Intermediate Similarity	NPC147232
0.7573	Intermediate Similarity	NPC295347
0.7573	Intermediate Similarity	NPC134067
0.7573	Intermediate Similarity	NPC53565
0.757	Intermediate Similarity	NPC271059
0.757	Intermediate Similarity	NPC476889
0.757	Intermediate Similarity	NPC25666
0.757	Intermediate Similarity	NPC194323
0.757	Intermediate Similarity	NPC275583
0.7568	Intermediate Similarity	NPC317107
0.7553	Intermediate Similarity	NPC321514
0.7551	Intermediate Similarity	NPC76333
0.7549	Intermediate Similarity	NPC477436
0.7549	Intermediate Similarity	NPC477435
0.7549	Intermediate Similarity	NPC199543
0.7547	Intermediate Similarity	NPC81530
0.7547	Intermediate Similarity	NPC472685
0.7547	Intermediate Similarity	NPC115862
0.7547	Intermediate Similarity	NPC474327
0.7547	Intermediate Similarity	NPC472643
0.7547	Intermediate Similarity	NPC472702
0.7544	Intermediate Similarity	NPC472934
0.7544	Intermediate Similarity	NPC243065
0.7526	Intermediate Similarity	NPC473592
0.7526	Intermediate Similarity	NPC105803
0.7525	Intermediate Similarity	NPC214844
0.7525	Intermediate Similarity	NPC51486
0.7524	Intermediate Similarity	NPC478056
0.7524	Intermediate Similarity	NPC174663
0.7524	Intermediate Similarity	NPC176845
0.7523	Intermediate Similarity	NPC112780
0.75	Intermediate Similarity	NPC235053
0.75	Intermediate Similarity	NPC1753
0.75	Intermediate Similarity	NPC327179
0.75	Intermediate Similarity	NPC469528
0.75	Intermediate Similarity	NPC24816
0.75	Intermediate Similarity	NPC90952
0.75	Intermediate Similarity	NPC48107
0.75	Intermediate Similarity	NPC4573
0.75	Intermediate Similarity	NPC317687
0.75	Intermediate Similarity	NPC307298
0.75	Intermediate Similarity	NPC213366
0.75	Intermediate Similarity	NPC40228
0.75	Intermediate Similarity	NPC118911
0.75	Intermediate Similarity	NPC477128
0.75	Intermediate Similarity	NPC472363
0.75	Intermediate Similarity	NPC476001
0.75	Intermediate Similarity	NPC474898
0.75	Intermediate Similarity	NPC474511
0.75	Intermediate Similarity	NPC21681
0.75	Intermediate Similarity	NPC154526
0.75	Intermediate Similarity	NPC327002
0.75	Intermediate Similarity	NPC472362
0.75	Intermediate Similarity	NPC469369
0.75	Intermediate Similarity	NPC132824
0.75	Intermediate Similarity	NPC472675
0.7477	Intermediate Similarity	NPC476081
0.7477	Intermediate Similarity	NPC119601
0.7477	Intermediate Similarity	NPC308726
0.7477	Intermediate Similarity	NPC470496
0.7477	Intermediate Similarity	NPC473036
0.7477	Intermediate Similarity	NPC272898
0.7476	Intermediate Similarity	NPC91010
0.7476	Intermediate Similarity	NPC470697
0.7476	Intermediate Similarity	NPC212812
0.7476	Intermediate Similarity	NPC477439
0.7475	Intermediate Similarity	NPC73038
0.7475	Intermediate Similarity	NPC470955
0.7475	Intermediate Similarity	NPC322159
0.7475	Intermediate Similarity	NPC220478
0.7475	Intermediate Similarity	NPC262085
0.7458	Intermediate Similarity	NPC91693
0.7458	Intermediate Similarity	NPC265557
0.7458	Intermediate Similarity	NPC18945
0.7458	Intermediate Similarity	NPC105926
0.7458	Intermediate Similarity	NPC67251
0.7456	Intermediate Similarity	NPC148458
0.7455	Intermediate Similarity	NPC476479
0.7455	Intermediate Similarity	NPC71220
0.7455	Intermediate Similarity	NPC137286
0.7455	Intermediate Similarity	NPC189075
0.7455	Intermediate Similarity	NPC151393
0.7455	Intermediate Similarity	NPC275539
0.7453	Intermediate Similarity	NPC472644
0.7453	Intermediate Similarity	NPC474012
0.7453	Intermediate Similarity	NPC198880
0.7453	Intermediate Similarity	NPC476299
0.7453	Intermediate Similarity	NPC474718
0.7453	Intermediate Similarity	NPC54705
0.7451	Intermediate Similarity	NPC49420
0.7451	Intermediate Similarity	NPC248913
0.7451	Intermediate Similarity	NPC174167
0.7451	Intermediate Similarity	NPC470036
0.7451	Intermediate Similarity	NPC38754
0.7438	Intermediate Similarity	NPC476854
0.7434	Intermediate Similarity	NPC25909
0.7434	Intermediate Similarity	NPC474271
0.7434	Intermediate Similarity	NPC122056
0.7431	Intermediate Similarity	NPC284365
0.7431	Intermediate Similarity	NPC472645
0.7431	Intermediate Similarity	NPC123726
0.7431	Intermediate Similarity	NPC477125
0.7431	Intermediate Similarity	NPC475414
0.7431	Intermediate Similarity	NPC173172
0.7429	Intermediate Similarity	NPC107243
0.7429	Intermediate Similarity	NPC23680
0.7429	Intermediate Similarity	NPC89225
0.7429	Intermediate Similarity	NPC474343
0.7429	Intermediate Similarity	NPC208094
0.7429	Intermediate Similarity	NPC187933
0.7429	Intermediate Similarity	NPC57416
0.7426	Intermediate Similarity	NPC36668
0.7426	Intermediate Similarity	NPC280833
0.7426	Intermediate Similarity	NPC118011
0.7426	Intermediate Similarity	NPC5509
0.7423	Intermediate Similarity	NPC474979
0.7414	Intermediate Similarity	NPC472933
0.7414	Intermediate Similarity	NPC268958
0.7411	Intermediate Similarity	NPC34315
0.7411	Intermediate Similarity	NPC472928
0.7411	Intermediate Similarity	NPC474871
0.7411	Intermediate Similarity	NPC260786
0.7411	Intermediate Similarity	NPC470246

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 NPC323441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1733
0.2-0.3	3822
0.3-0.4	2209
0.4-0.5	759
0.5-0.6	215
0.6-0.7	185
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7549	Intermediate Similarity	NPD6399	Phase 3
0.7524	Intermediate Similarity	NPD5696	Approved
0.7297	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD5739	Approved
0.7273	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6675	Approved
0.7273	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7264	Intermediate Similarity	NPD7902	Approved
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7255	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD6372	Approved
0.7157	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7129	Intermediate Similarity	NPD6098	Approved
0.7129	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6411	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.7087	Intermediate Similarity	NPD6080	Approved
0.7087	Intermediate Similarity	NPD6904	Approved
0.7087	Intermediate Similarity	NPD6673	Approved
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7054	Intermediate Similarity	NPD5697	Approved
0.7054	Intermediate Similarity	NPD5701	Approved
0.7041	Intermediate Similarity	NPD4695	Discontinued
0.7018	Intermediate Similarity	NPD6883	Approved
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD7290	Approved
0.6991	Remote Similarity	NPD6011	Approved
0.6981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD6869	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6957	Remote Similarity	NPD6847	Approved
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7515	Phase 2
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6101	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6916	Remote Similarity	NPD4629	Approved
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6882	Approved
0.6897	Remote Similarity	NPD8297	Approved
0.6893	Remote Similarity	NPD3573	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.6881	Remote Similarity	NPD7638	Approved
0.6881	Remote Similarity	NPD4225	Approved
0.6863	Remote Similarity	NPD1694	Approved
0.6863	Remote Similarity	NPD5329	Approved
0.6852	Remote Similarity	NPD7614	Phase 1
0.6818	Remote Similarity	NPD7640	Approved
0.6818	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD5281	Approved
0.6792	Remote Similarity	NPD5284	Approved
0.6792	Remote Similarity	NPD6050	Approved
0.6789	Remote Similarity	NPD4755	Approved
0.6765	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD4753	Phase 2
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6053	Discontinued
0.6733	Remote Similarity	NPD3667	Approved
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5692	Phase 3
0.6697	Remote Similarity	NPD7732	Phase 3
0.6697	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6639	Remote Similarity	NPD6319	Approved
0.6638	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5694	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD8035	Phase 2
0.6635	Remote Similarity	NPD3618	Phase 1
0.6635	Remote Similarity	NPD4519	Discontinued
0.6635	Remote Similarity	NPD4623	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD6335	Approved
0.6609	Remote Similarity	NPD6614	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6604	Remote Similarity	NPD6051	Approved
0.6604	Remote Similarity	NPD5328	Approved
0.6585	Remote Similarity	NPD6921	Approved
0.6583	Remote Similarity	NPD6274	Approved
0.6579	Remote Similarity	NPD5141	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.656	Remote Similarity	NPD7492	Approved
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD6686	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5222	Approved
0.6545	Remote Similarity	NPD5221	Approved
0.6545	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5785	Approved
0.6529	Remote Similarity	NPD6317	Approved
0.6514	Remote Similarity	NPD6001	Approved
0.6512	Remote Similarity	NPD7260	Phase 2
0.6509	Remote Similarity	NPD5208	Approved
0.6508	Remote Similarity	NPD6616	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6504	Remote Similarity	NPD6054	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6491	Remote Similarity	NPD4754	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5173	Approved
0.6481	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD5280	Approved
0.6476	Remote Similarity	NPD4694	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6475	Remote Similarity	NPD6313	Approved
0.6475	Remote Similarity	NPD6314	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7078	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6455	Remote Similarity	NPD5654	Approved
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6908	Approved
0.6452	Remote Similarity	NPD6909	Approved
0.6446	Remote Similarity	NPD6868	Approved
0.6442	Remote Similarity	NPD3668	Phase 3
0.6442	Remote Similarity	NPD3666	Approved
0.6442	Remote Similarity	NPD3133	Approved
0.6442	Remote Similarity	NPD3665	Phase 1
0.6441	Remote Similarity	NPD4634	Approved
0.6441	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD4202	Approved
0.6406	Remote Similarity	NPD7736	Approved
0.6404	Remote Similarity	NPD5091	Approved
0.6404	Remote Similarity	NPD7632	Discontinued
0.64	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD6009	Approved
0.6389	Remote Similarity	NPD5207	Approved
0.6379	Remote Similarity	NPD4767	Approved
0.6379	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD8039	Approved
0.6357	Remote Similarity	NPD7319	Approved
0.6356	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7604	Phase 2
0.6339	Remote Similarity	NPD5959	Approved
0.6336	Remote Similarity	NPD6845	Suspended
0.633	Remote Similarity	NPD7637	Suspended
0.6321	Remote Similarity	NPD5279	Phase 3
0.6321	Remote Similarity	NPD4689	Approved
0.6321	Remote Similarity	NPD4688	Approved
0.6321	Remote Similarity	NPD5786	Approved
0.6321	Remote Similarity	NPD4690	Approved
0.6321	Remote Similarity	NPD5205	Approved
0.6321	Remote Similarity	NPD4693	Phase 3
0.6321	Remote Similarity	NPD4138	Approved
0.632	Remote Similarity	NPD6016	Approved
0.632	Remote Similarity	NPD6015	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.6311	Remote Similarity	NPD5369	Approved
0.6271	Remote Similarity	NPD4729	Approved
0.6271	Remote Similarity	NPD5128	Approved
0.6271	Remote Similarity	NPD4730	Approved
0.627	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1696	Phase 3
0.6226	Remote Similarity	NPD7520	Clinical (unspecified phase)

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