NPASS Compound

Natural Product: NPC230564

Natural Product ID	NPC230564
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SYYVXQOWLOEXDU-WFFVHEBKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11506296
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 80 84 0 0 0 0 0 0 0 0999 V2000 -9.6615 3.4954 3.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2474 2.7010 2.3831 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5808 1.6773 1.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7131 0.4317 2.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0660 -0.7489 1.6233 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2258 -0.4266 0.4480 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1252 0.9634 0.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7373 1.9565 0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5404 3.7590 -0.0360 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.8230 -1.0299 0.5806 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5480 -1.4402 -0.8092 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6645 -1.5234 -1.4282 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.7328 -1.2196 -0.6465 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2371 -1.7232 -1.4274 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2255 -1.6053 -0.7312 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1283 -2.1151 -2.7639 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9445 -2.4020 -3.5206 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0838 -1.2435 -3.7754 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4692 -0.4243 -2.7595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5272 -0.8116 -1.8476 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2520 -1.2587 -2.0934 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1535 -2.5461 -2.1015 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4860 -2.9025 -2.3781 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4444 -1.9615 -2.6510 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8322 -2.3492 -2.9621 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6930 -2.5601 -1.7690 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7884 -1.3477 -0.9875 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5861 -1.3189 0.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1905 -2.3607 0.5694 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6650 -0.0856 0.9867 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1121 1.0383 0.7647 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4521 1.9588 1.7556 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7732 1.5589 2.1902 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0559 2.0625 3.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1539 2.6997 3.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1509 2.9213 2.7848 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9691 2.4961 1.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7735 1.7807 1.1452 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1037 0.5407 0.5369 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3077 2.8087 0.2057 Br 0 0 0 0 0 0 0 0 0 0 0 0 10.3468 3.5975 3.0507 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5293 2.8100 3.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4972 3.3516 5.5848 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.4815 0.0304 2.2460 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0373 -0.6439 -2.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7394 -0.2905 -2.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 1.5291 -2.3643 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.0308 -3.9621 -1.6358 Br 0 0 0 0 0 0 0 0 0 0 0 0 -8.2987 -1.3334 2.6520 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8554 0.1894 3.7227 Br 0 0 0 0 0 0 0 0 0 0 0 0 -10.4206 4.2234 3.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2443 2.8800 4.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8689 4.1352 2.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8445 -1.5143 1.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4758 1.1621 -0.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1040 -0.2365 0.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8121 -1.8441 1.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0618 -2.2085 -3.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4042 -3.2044 -2.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2520 -2.8318 -4.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6829 -0.5198 -4.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -1.5359 -4.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2488 0.2259 -2.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 0.4698 -3.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 -3.9480 -2.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8907 -3.2816 -3.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3223 -1.5290 -3.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2156 -3.3803 -1.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7012 -2.9515 -2.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3212 -0.4461 -1.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3544 1.9361 4.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2456 2.4014 0.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2915 0.7458 -0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3947 3.4518 3.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7394 2.2131 2.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3908 2.0915 4.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8362 -0.2009 3.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4131 -0.5368 2.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7847 0.1328 -2.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8455 -0.6225 3.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 33 32 1 6 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 41 42 1 0 35 43 1 0 33 44 1 0 24 45 1 0 45 46 2 0 46 47 1 0 22 48 1 0 5 49 1 0 4 50 1 0 8 3 1 0 46 21 1 0 6 13 1 6 44 30 1 0 38 33 1 0 1 51 1 0 1 52 1 0 1 53 1 0 5 54 1 6 7 55 1 0 10 56 1 0 10 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 23 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 34 71 1 0 38 72 1 6 39 73 1 0 42 74 1 0 42 75 1 0 42 76 1 0 44 77 1 0 44 78 1 0 45 79 1 0 49 80 1 0 M END

Standard InCHIKey	SYYVXQOWLOEXDU-WFFVHEBKSA-N
Standard InCHI	InChI=1S/C31H30Br6N4O9/c1-46-24-17(34)10-30(26(42)21(24)36)12-19(40-49-30)28(44)38-5-3-7-48-23-15(32)8-14(9-16(23)33)4-6-39-29(45)20-13-31(50-41-20)11-18(35)25(47-2)22(37)27(31)43/h8-11,26-27,42-43H,3-7,12-13H2,1-2H3,(H,38,44)(H,39,45)/t26-,27+,30+,31-/m0/s1
SMILES	COC1=C([C@@H]([C@@]2(C=C1Br)CC(=NO2)C(=O)NCCCOc1c(cc(CCNC(=O)C2=NO[C@@]3(C=C(C(=C([C@H]3O)Br)OC)Br)C2)cc1Br)Br)O)Br

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1075.71	Volume:	711.749 ? Van der Waals volume.
Dense:	1.511	LogP:	4.228 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.284 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.476 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	30.0
TPSA:	169.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.195	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.812	Fsp³:	0.419
MCE-18:	158.091 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.998	Fluc inhibitor:	0.158 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.279 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.658 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.36	Promiscuous compounds:	0.036

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.912	MDCK Permeability:	-4.788
Pgp-inhibitor:	0.484	Pgp-substrate:	0.074
PAMPA:	0.003 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.013	30% Bioavailability (F30%):	0.116
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083	MRP1:	1.0
Plasma Protein Binding (PPB):	97.209%	Volume Distribution (VD):	-0.196
Fu:	1.968% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.897
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.989
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.122 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.583

Half-life (T1/2):

4.25

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.33
Human Hepatotoxicity (H-HT):	0.189	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	1.0	Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	1.0	Eye Corrosion:	0.0
Eye Irritation:	0.229	Respiratory Toxicity:	0.983
Drug-induced Neurotoxicity:	0.954	Ototoxicity:	0.573
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.761
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.112	Hek293 Cytotoxicity:	0.989
BCF:	1.812 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.768 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.553 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.902 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096858]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543904]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277747]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720523]
NPO287	Wrightia javanica	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12808258]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599257]
NPO1512	Cissampelos fasciculata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8123	Aplysina cavernicola	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9047.1	Brassica rapa subsp. oleifera	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1594	[enterobacter] aerogenes	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9047.1	Brassica rapa subsp. oleifera	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO287	Wrightia javanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9047.1	Brassica rapa subsp. oleifera	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3434	Thymus camphoratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27875	Fallopia convolvulus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1594	[enterobacter] aerogenes	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9047.1	Brassica rapa subsp. oleifera	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO287	Wrightia javanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3266	Euryops sulcatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2651	Ceroplastes floridensis	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8123	Aplysina cavernicola	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4191	Thermococcus acidaminovorans	Species	Thermococcaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO6725	Tulipa hybrid	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8290	Mycena megaspora	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6901	Lophosoria quadripinnata	Species	Dicksoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7223	Castela tortuosa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1512	Cissampelos fasciculata	Species	Menispermaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC230564 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17263
0.1-0.2	32311
0.2-0.3	203
0.3-0.4	16
0.4-0.5	20
0.5-0.6	19
0.6-0.7	9
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202866
0.8519	High Similarity	NPC603425
0.85	High Similarity	NPC77435
0.85	High Similarity	NPC259071
0.8313	Intermediate Similarity	NPC606574
0.8182	Intermediate Similarity	NPC603698
0.8125	Intermediate Similarity	NPC483876
0.8125	Intermediate Similarity	NPC600925
0.8	Intermediate Similarity	NPC611077
0.7907	Intermediate Similarity	NPC607100
0.7826	Intermediate Similarity	NPC606635
0.7614	Intermediate Similarity	NPC609979
0.7558	Intermediate Similarity	NPC480151
0.747	Intermediate Similarity	NPC607066
0.7391	Intermediate Similarity	NPC227953
0.7125	Intermediate Similarity	NPC487872
0.7125	Intermediate Similarity	NPC608122
0.6867	Remote Similarity	NPC487873
0.6552	Remote Similarity	NPC487915
0.6522	Remote Similarity	NPC147847
0.6477	Remote Similarity	NPC487914
0.6477	Remote Similarity	NPC489611
0.6477	Remote Similarity	NPC604329
0.6344	Remote Similarity	NPC174607
0.6064	Remote Similarity	NPC489612
0.6053	Remote Similarity	NPC1702
0.5897	Remote Similarity	NPC158672
0.5679	Remote Similarity	NPC487917
0.5568	Remote Similarity	NPC600759
0.5529	Remote Similarity	NPC473262
0.5529	Remote Similarity	NPC202166
0.5455	Remote Similarity	NPC304257
0.5444	Remote Similarity	NPC201900
0.5402	Remote Similarity	NPC473261
0.5402	Remote Similarity	NPC300912
0.5341	Remote Similarity	NPC313173
0.5333	Remote Similarity	NPC66855
0.5333	Remote Similarity	NPC181086
0.5326	Remote Similarity	NPC608121
0.5312	Remote Similarity	NPC601097
0.5227	Remote Similarity	NPC145149
0.5111	Remote Similarity	NPC260270
0.5055	Remote Similarity	NPC470886
0.505	Remote Similarity	NPC121571
0.505	Remote Similarity	NPC8093

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC230564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3089
0.1-0.2	6031
0.2-0.3	30
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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